Pyridine ketones useful as herbicides

ABSTRACT

Compounds of formula (I) in which the substituents are as defined in claim 1 are suitable for use as herbicides.

This application is a Continuation of PCT/EP99/06761 filed Sep. 13,1999.

The present invention relates to novel herbicidally active pyridineketones, to processes for their preparation, to compositions whichcomprise these compounds, and to their use for controlling weeds, inparticular in crops of useful plants, or for inhibiting plant growth.

Pyridine ketones having herbicidal action are described, for example, inWO 97/46530. We have now found novel pyridine ketones having herbicidaland growth-inhibiting properties.

The present invention thus provides compounds of the formula I

in which

each R independently is C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl,C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,C₁-C₆haloalkylsulfonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyl,C₁-C₆alkylamino, di-C₁-C₆alkylamino, C₁-C₆alkylaminosulfonyl,di-C₁-C₆alkylaminosulfonyl, —N(R₁)—S—R₂, —N(R₃)—SO—R₄, —N(R₅)—SO₂—R₆,nitro, cyano, halogen, hydroxy, amino, formyl, hydroxy-C₁-C₆alkyl,C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkoxycarbonyloxy-C₁-C₆alkyl,C₁-C₆alkylthio-C₁-C₆alkyl, C₁-C₆alkylsulfinyl-C₁-C₆alkyl,C₁-C₆alkylsulfonyl-C₁-C₆alkyl, thiocyanato-C₁-C₆alkyl, cyano-C₁-C₆alkyl,oxiranyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, C₁-C₆alkoxy-C₁-C₆alkoxy,cyano-C₁-C₆alkenyloxy, C₁-C₆alkoxycarbonyloxy-C₁-C₆alkoxy,C₃C₆alkynyloxy, cyano-C₁-C₆alkoxy, C₁-C₆ alkoxycarbonyl-C₁-C₆alkoxy,C₁-C₆alkylthio-C₁-C₆alkoxy, alkoxycarbonyl-C₁-C₆alkylthio,alkoxycarbonyl-C₁-C₆alkylsulfinyl, alkoxycarbonyl-C₁-C₆alkylsulfonyl,C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy, phenyl, benzyl,phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, benzylthio,benzylsulfinyl or benzylsulfonyl, where the phenyl groups may be mono-or polysubstituted by halogen, methyl, ethyl, trifluoromethyl, methoxyor nitro, or R is a five- to ten-membered monocyclic or fused bicyclicring system, which may be aromatic or partially saturated and maycontain 1 to 4 heteroatoms selected from the group consisting ofnitrogen, oxygen and sulfur, where the ring system is either attacheddirectly to the pyridine ring or attached to the pyridine ring via aC₁-C₄alkylene group, and where each ring system may not contain morethan 2 oxygen atoms and not more than two sulfur atoms, and where thering system for its part may be mono-, di- or trisubstituted byC₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio,C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio,C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio,C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl,C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl,aminosulfonyl, C₁-C₆alkylaminosulfonyl, C₁-C₆dialkylaminosulfonyl,C₁-C₆alkylene-R₇, NR₈R₉, halogen, cyano, nitro, phenyl and benzylthio,where phenyl and benzylthio for their part may be substituted on thephenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy,halogen, cyano or nitro, and where substituents on the nitrogen in theheterocyclic ring are different from halogen;

m is 1, 2, 3 or 4;

p is 0 or 1;

R₁, R₃ and R₅ independently of one another are hydrogen or C₁-C₆alkyl;

R₂ is NR₁₀R₁₁, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl,C₃-C₆cycloalkyl or phenyl, where phenyl for its part may be substitutedby C₁-C₃alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₃haloalkoxy, halogen,cyano or nitro;

R₄ is NR₁₂R₁₃, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl,C₃-C₆cycloalkyl or phenyl, where phenyl for its part may be substitutedby C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen,cyano or nitro;

R₆ is NR₁₄R₁₅, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl,C₃-C₆cycloalkyl or phpnyl, where phenyl for its part may be substitutedby C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen,cyano or nitro;

R₇ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for itspart may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro;

R₈, R₁₀, R₁₂ and R₁₄ independently of one another are hydrogen orC₁-C₆alkyl;

R₉, R₁₁, R₁₃ and R₁₅ is independently of one another are C₁-C₆alkyl orC₁-C₆alkoxy;

Q is the group Q₁

in which

R₁₆, R₁₇, R₁₈ and R₁₉ independently of one another are hydrogen,hydroxyl, C₁-C₄alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₄alkoxycarbonyl,C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₄alkyl-NHS(O)₂, C₁-C₄haloalkyl, —NH—C₁-C₄alkyl, —N(C₁-C₄alkyl)₂,C₁-C₆alkoxy, cyano, nitro, halogen or phenyl, which for its part may besubstituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino,di-C₁-C₄alkylamino, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio,C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O,C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro, COOHor cyano; or two adjacent substituents from the group consisting of R₁₆,R₁₇, R₁₈ and R₁₉ form a C₂-C₆alkyiene bridge;

R₂₀ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy,C₁-C₄alkoxycarbonyl-C₁-C₄alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl,C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl,C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio,C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl,C₂-C₁₂alkenylthio, C₂-C₁₂alkeny isulfinyl, C₂-C₁₂alkenylsulfonyl,C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl,C₂-C₁₂haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl,C₂-C₁₂haloalkenylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O,C₁-C₄alkyl-(C₁-C₄alkoxy)P(Q)O, H(C₁-C₄alkoxy)P(O)O,

R₃₇R₃₈N, R₇₁R₇₂NNH—, R₇₃R₇₄NC(O)NH—, C₁-C₄alkyl-S(O)₃₉,C₁-C₄haloalkyl-S(O)₂NR₄₀, C₁-C₆alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O,C₁-C₁₈alkylcarbonyloxy, where the alkyl group may be substituted byhalogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, C₂-C₁₈alkenylcarbonyloxy,C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy,C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy,C₁-C₁₂alkylthiocarbamoyl, C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)—NH—,di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)-NH—, benzyloxy, benzylthio,benzylsulfinyl, benzyisulfonyl, phenoxy, phenylthio, phenylsulfinyl,phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groupsfor their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio,C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O,C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro orcyano,

or a group Ar₁-thio, Ar₂-sulfinyl, Ar₃-sulfonyl, —OCO—Ar₄ or NH—Ar_(s)in which Ar₁, Ar₂, Ar₃, Ar₄ and Ar₅ independently of one another are afive- to ten-membered monocyclic or fused bicyclic ring system which maybe aromatic or partially saturated and may contain 1 to 4 heteroatomsselected from the group consisting of nitrogen, oxygen and sulfur, andin which each ring system may not contain more than 2 oxygen atoms andnot more than two sulfur atoms, and in which the ring system for itspart may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy,mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio,C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio,C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio,C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosufonyl,C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₄₁, NR₄₂R₄₃, halogen, cyano,nitro, phenyl and benzylthio, where phenyl and benzylthio for their partmay be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and wheresubstituents on the nitrogen in the heterocyclic ring are different fromhalogen;

R₄₁ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for itspart may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro;

R₄₂ is hydrogen or C₁-C₆alkyl;

R₄₃ is C₁-C₆alkyl or C₁-C₆alkoxy;

R₂₁, R₃₇, R₃₉, R₄₀, R₇₁ and R₇₃ independently of one another arehydrogen or C₁-C₄alkyl;

R₂₂, R₃₈, R₇₂ and R₇₄ independently of one another are hydrogen,C₁-C₁₂alkyl, hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy;or R₂₁ and R₂₂ together or R₃₇ and R₃₈ together or R₇₁ and R₇₂ togetheror R₇₃ and R₇₄ together are pyrrolidino, piperidino, morpholino,thiomorpholino, which may be mono- or polysubstituted by methyl groups;or are the group Q₂

in which

Y is a chemical bond, an alkylene group A₁, carbonyl, oxygen, sulfur,sulfinyl, sulfonyl, —NHR₂₄₈ or NH(CO)R₂₄₉;

A₁ is C(R₂₄₆R₂₄₇)m₀₁;

A is C(R₂₄₄R₂₄₅)r;

r and m₀₁ independently of one another are 1 or 2;

R₂₄₀ is hydrogen, methyl or C₁-C₃alkoxycarbonyl;

R₂₄₁, R₂₄₂, R₂₄₃, R₂₄₄, R₂₄₅, R₂₄₆ and R₂₄₇ independently of one anotherare hydrogen, halogen or methyl, or R₂₄₃ together with an adjacent groupR₂₄₅ or R₂₄₇ is a chemical bond;

R₂₄₈ and R₂₄₉ independently of one another are hydrogen or C₁-C₄alkyl;

R₂₃ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy,C₁-C₄alkoxycarbonyl-C₁-C₄alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl,C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl,C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio,C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl,C₂-C₁₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂alkenyisulfonyl,C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl,C₂-C₁₂haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl,C₂-C₁₂haloalkenylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsuflonyl, (C₁-C₄alkoxy)₂P(O)O,C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O,

R₄₄R₄₅N, R₇₅R₇₆NNH—, R₄₆R₄₇NC(O)O—, R₇₇R₇₈NC(O)NH—,C₁-C₄alkyl-S(O)₂NR₄₈, C₁-C₄haloalkyl-S(O)₂NR₄₉, C₁-C₄alkyl-S(O)₂O,C₁-C₄haloalkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, where the alkyl group maybe substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano,C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy,C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy,C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl,C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)—NH—,di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)—NH—, benzyloxy, benzylthio,benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl,phenyisulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groupsfor their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio,C₁-C₄haloalkyisulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O,C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro orcyano,

or a group Ar₆-thio, Ar₇-sulfinyl, Ar₈-sulfonyl, —OCO—Ar₉ or NH—Ar₁₀ inwhich Ar₆, Ar₇, Ar₈, Ar₉ and Ar₁₀ independently of one another are afive- to ten-membered monocyclic or fused bicyclic ring system which maybe aromatic or partially saturated and may contain 1 to 4 heteroatomsselected from the group consisting of nitrogen, oxygen and sulfur, andin which each ring system may not contain more than 2 oxygen atoms andnot more than two sulfur atoms, and in which the ring system for itspart may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy,mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio,C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio,C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio,C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl,C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₅₀, NR₅₁R₅₂, halogen, cyano,nitro, phenyl and benzylthio, where phenyl and benzylthio for their partmay be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and wheresubstituents on the nitrogen in the heterocyclic ring are different fromhalogen;

R₅₀ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for itspart may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro;

R₅₁ is hydrogen or C₁-C₆alkyl;

R₅₂ is C₁-C₆alkyl or C₁-C₆alkoxy;

R₄₆, R₄₄, R₄₈, R₄₉, R₇₅ and R₇₇ independently of one another arehydrogen or C₁-C₄alkyl;

R₄₇, R₄₅, R₇₆ and R₇₈ independently of one another are hydrogen,C₁-C₁₂alkyl, hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy;or R₄₄ and R₄₅ together or R₄₆ and R₄₇ together or R₇₅ and R₇₆ togetheror R₇₇ and R₇₈ together are pyrrolidino, piperidino, morpholino,thiomorpholino, which may be mono- or polysubstituted by methyl groups;or are the group Q₃

in which

R₂₆ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂ alkoxy,C₁-C₄alkoxycarbonyl-C₁-C₄alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl,C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl,C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio,C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl,C₂-C₁₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂alkenylsulfonyl,C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl,C₂-C₁₂haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl,C₂-C₁₂haloalkenylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O,C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O,

R₅₃R₅₄N, R₇₉R₈₀NNH—, R₅₅R₅₆NC(O)O—, R₈₁R₈₂NC(O)NH—,C₁-C₄alkyl-S(O)₂NR₅₇, C₁-C₄haloalkyl-S(O)₂NR₅₈, C₁-C₄alkyl-S(O)₂O,C₁-C₄haloalkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, where the alkyl group maybe substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano,C₂C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy,C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy,C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl,C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)—NH—,di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)—NH—, benzyloxy, benzyithio,benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl,phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groupsfor their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio,C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O,C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro orcyano,

or a group Ar₁₁-thio, Ar₁₂-sulfinyl, Ar₁₃-sulfonyl, —OCO—Ar₁₄ or NH—Ar₁₅in which Ar₁₁, Ar₁₂, Ar₁₃, Ar₁₄ and Ar₁₅ independently of one anotherare a five- to ten-membered monocyclic or fused bicyclic ring systemwhich may be aromatic or partially saturated and may contain 1 to 4heteroatoms selected from the group consisting of nitrogen, oxygen andsulfur, and in which each ring system may not contain more than 2 oxygenatoms and not more than two sulfur atoms, and in which the ring systemfor its part may be mono-, di- or trisubstituted by C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl,C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy,C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio,C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio,C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl,C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl,aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl,C₁-C₃alkylene-R₅₉, NR₆₀R₆₁, halogen, cyano, nitro, phenyl andbenzylthio, where phenyl and benzylthio for their part may besubstituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and wheresubstituents on the nitrogen in the heterocyclic ring are different fromhalogen;

R₅₉ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for itspart may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro;

R₆₀ is hydrogen or C₁-C₆alkyl;

R₆₁ is C₁-C₆alkyl or C₁-C₆alkoxy;

R₅₅, R₅₃, R₅₇, R₅₈, R₇₉ and R₈₁ independently of one another arehydrogen or C₁-C₄alkyl;

R₅₆, R₅₄, R₈₀ and R₈₂ independently of one another are hydrogen,C₁-C₁₂alkyl, hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy;or R₅₃ and R₅₄ together or R₅₅ and R₅₆ together or R₇₉ and R₈₀ togetheror R₈₁ and R₈₂ together are pyrrolidino, piperidino, morpholino,thiomorpholino, which may be mono- or polysubstituted by methyl groups;

R₂₉ is hydrogen, C₁-C₆alkyl, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,(C₁-C₄alkyl)NHCO, phenylaminocarbonyl, benzylaminocarbonyl or(C₁-C₄alkyl)₂NCO, where the phenyl and benzyl groups for their part mayeach be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio,C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O,C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro orcyano;

or is the group Q₄

in which

R₃₀ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy,C₁-C₄alkoxycarbonyl-C₁-C₄alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl,C₁-C₁₂alky lsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl,C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio,C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl,C₂-C₁₂alkenylthio, C₂-C₁₂alkenyisulfinyl, C₂-C₁₂alkenylsulfonyl,C₂-C₁₂alkynylthio, C₂-C₁₂alkynyisulfinyl, C₂-C₁₂alkynyisulfonyl,C₂-C₁₂haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl,C₂-C₁₂haloalkenylsuffonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O,C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O,

R₆₂R₆₃N, R₈₃R₈₄NNH—, R₆₄R₆₅NC(O)O—, R₈₅R₈₆NC(O)NH—,C₁-C₄alkyl-S(O)₂NR₆₆, C₁-C₄haloalkyl-S(O)₂NR₆₇, C₁-C₄alkyl-S(O)₂O,C₁-C₄haloalkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, where the alkyl group maybe substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano,C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy,C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy,C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl,C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)NH—, di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)—NH—,benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, phenoxy,phenylthio, phenylsulfinyl, phenylsulfonyl, phenyisulfonyloxy orbenzoyloxy, where the phenyl groups for their part may each besubstituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino,di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfony l, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, Ci-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O,C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro orcyano,

or a group Ar₁₆-thio, Ar₁₇-sulfinyl, Ar₁₈-sulfonyl, —OCO—Ar₁₉ or NH—Ar₂₀in which Ar₁₆, Ar₁₇, Ar₁₈, Ar₁₉ and Ar₂₀ independently of one anotherare a five- to ten-membered monocyclic or fused bicyclic ring systemwhich may be aromatic or partially saturated and may contain 1 to 4heteroatoms selected from the group consisting of nitrogen, oxygen andsulfur, and in which each ring system may not contain more than 2 oxygenatoms and not more than two sulfur atoms, and in which the ring systemfor its part may be mono-, di- or trisubstituted by C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl,C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy,C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio,C₂-C₅alkoxyalkylthio, C₃-C₅acety oalkylthio,C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl,C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl,aminosulfonyl, C₁-C₂alkylaminosulfony l, C₂-C₄dialkylaminosulfonyl,C₁-C₃alkylene-R₆₈, NR₆₉R₇₀, halogen, cyano, nitro, phenyl andbenzylthio, where phenyl and benzylthio for their part may besubstituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and wheresubstituents on the nitrogen in the heterocyclic ring are different fromhalogen;

R₆₈ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for itspart may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro;

R₇₀ is hydrogen or C₁-C₆alkyl;

R₆₁ is C₁-C₆alkyl or C₁-C₆alkoxy;

R₆₄, R₆₂, R₆₆, R₆₇, R₈₃ and R₈₅ independently of one another arehydrogen or C₁-C₄alkyl;

R₆₅, R₆₃, R₈₄ and R₈₆ independently of one another are hydrogen,C₁-C₁₂alkyl, hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy;or R₆₂ and R₆₃ together or R₆₄ and R₆₅ together or R₈₃ and R₈₄ togetheror R₈₅ and R₈₆ together are pyrrolidino, piperidino, morpholino,thiomorpholino, which may be mono- or polysubstituted by methyl groups;

R₃₃ and R₃₄ independently of one another are hydrogen, C₁-C₄alkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₄alkoxycarbonyl, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₄alkyl-NHS(O)₂,C₁-C₄haloalkyl, —NH—C₁-C₄alkyl, —N(C₁-C₄alkyl)₂, C₁-C₆alkoxy or phenyl,which for its part may be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₄alkyl-S(O)₂O,C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl,C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH,C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro, COOH or cyano; or R₃₃ andR₃₄ together form a C₂-C₆alkylene bridge; and

R₃₅ is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl or benzyl, whichfor its part may be substituted by halogen, methyl or methoxy, or isC₁-C₄alkoxycarbonyl or phenyl, which for its part may be substituted byC₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄aikoxy, C₁-C₄haloalkoxy,C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino,di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio,C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsuifonyl, C₁-C₄haloalkyl-S(O)₂O,C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro, COOHor cyano;

or is the group Q₅

in which

Z is S, SO or SO₂;

R₀₁ is hydrogen, C₁-C₈alkyl, C₁-C₈alkyl substituted by halogen,C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl, C₁-C₄alkylsulfinyl,—CO₂R₀₂, —COR₀₃, —COSR₀₄, —NR₀₅R₀₆, CONR₀₃₆R₀₃₇ or phenyl, which for itspart may be substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy,C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl,C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl,(C₁-C₄alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl,(C₁-C₄alkylsulfonyl)-C₁-C₄alkyl, NHS)₂—C₁-C₄alkyl, NHSO₂-phenyl,N(C₁-C₆alkyl)S)₂—C₁-C₄alkyl, N(C₁-C₆alkyl)SO₂-phenyl,N(C₂-C₆alkenyl)S)₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl,N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyt,N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl, N(C₃-C₇cycloalkyl)SO₂-phenyl,N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OSO₂—C₁-C₄alkyl,CONR₂₅R₂₆, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio,C₁-C₄haloalkylthio, phenytthio, C₁-C₄alkylsulfonyl,C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl,C₁-C₄haloalkylsulfinyl, phenylsulfinyl, C₁-C₄alkylene-phenyl or—NR₀₁₅CO₂R₀₂₇;

or R₀₁ is C₂-C₈alkenyl or C₂-C₈alkenyl substituted by halogen,C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl, C₁-C₄alkylsulfinyl,—CONR₀₃₂R₀₃₃, cyano, nitro, —CHO, —CO₂R₀₃₈, —COR₀₃₉, —COS—C₁-C₄alkyl,—NR₀₃₄R₀₃₅ or phenyl which for its part may be substituted byC₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl,C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano,—COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl,NHSO)₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl,N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl,N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl, alkyl,N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl,N(phenyl)SO₂-phenyl, OSO₂—C₁-C₄alkyl, CONR₀₄₀R₀₄₁, OSO₂—C₁-C₄haloalkyl,OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl,C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsuffinyl,C₁-C₄alkylene-phenyl or —NR₀₄₃CO₂R₀₄₂;

or R₀₁ is C₃-C₆alkynyl or C₃-C₆alkynyl substituted by halogen,C₁-C₄haloalkyl, cyano, —CO₂R₀₄₄ or phenyl, which for its part may besubstituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen,nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl,N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl,N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl,N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl,N(phenyl)SO₂-phenyt, OSO₂—C₁-C₄alkyl, CONR₀₂₈R₀₂₉, OSO₂—C₁-C₄haloalkyl,OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsu ifonyl, phenylsulfonyl,C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl,C₁-C₄alkylene-phenyl or —NR₀₃₁CO₂R₀₃₀;

or R₀₁ is C₃-C₇cycloalkyl, C₃-C₇cycloalkyl substituted by C₁-C₄alkyl,C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl orphenyl, which for its part may be substituted by halogen, nitro, cyano,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,C₁-C₄alkyl and C₁-C₄haloalkyl; or

R₀₁ is C₁-C₄alkylene-C₃-C₇cycloalkyl, phenyl, or phenyl which issubstituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen,nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl,N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl,N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl,N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl,N(phenyl)SO₂-phenyl, OSO₂—C₁-C₄alkyl, CONR₀₄₅R₀₄₆, OSO₂—C₁-C₄haloalkyl,OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsutfonyl,C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, or—NR₀₄₈CO₂R₀₄₇; or

R₀₁ is C₁-C₄alkylene-phenyl, COR₀₇ or 4-6-membered heterocyclyl;

R₀₂, R₀₃₈, R₀₄₄ and R₀₆₆ independently of one another are hydrogen,C₁-C₄alkyl, phenyl, or phenyl which is substituted by C₁-C₄alkyl,C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl,C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano,—COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂-C₁-C₄alkyl,N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl,N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂-C₁-C₄alkyl, N(C₃-Ccycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl,OSO₂—C₁-C₄alkyl, CONR₀₄₉R₀₅₀, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl,C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsuffonyl,C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl,C₁-C₄haioalkylsulfinyl, phenylsultinyl, C₁-C₄alkylene phenyl or—NR₀₅₂CO₂R₀₅₃;

R₀₃, R₀₃₉ and R₀₆₇ independently of one another are C₁-C₄alkyl, phenylor phenyl which is substituted by C₁-C₄alkyl, C₁-C₆haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl,C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH,COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl,N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl,N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇ cycloalkyl)SO₂—C₁-C₄alkyl,N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl,N(phenyl)SO₂-phenyl, OSO₂—C₁-C₄alkyl, CONRO₀₇₀R₀₅₄, OSO₂—C₁-C₄haloalkyl,OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl,C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl,C₁-C₄alkylene-phenyl or —NR₀₅₆CO₂R₀₅₅;

R₀₄ is C₁-C₄alkyl;

R₀₅ is hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl,C₃-C₇cycloalkyl, phenyl or phenyl which is substituted by C₁-C₄alkyl,C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl,C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano,—COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl,N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂H,N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl,N(C₃-C₇cycloalkyl)SO₂H, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl,N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl,N(phenyl)SO₂-phenyl, OSO₂-C₁-C₄alkyl, CONR₀₅₇R₀₅₈, OSO₂—C₁-C₄haloalkyl,OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio,C₁-C₄alkylsulfonyi, C₁-C₄haloalkylsulfonyl, phenylsulfonyl,C₁-C₄alkyisulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl,C₁-C₄alkylenephenyl or —NR₀₆₀CO₂R₀₅₉;

R₀₆ is hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl,C₃-C₇cycloalkyl, phenyl or phenyl which is substituted by C₁-C₄aikyl,C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl,C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano,—COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl,N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl,N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl,N(C₃-C₇cycloaikyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl,N(phenyl)SO₂-phenyl, OSO₂-C₁-C₄alkyl, CONR₀₆₁R₀₆₂, OSO₂—C₁-C₄ haloalkyl,OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl,C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl,C₁-C₄alkylene-phenyl or —NR₀₆₄CO₂R₀₆₃;

R₀₇ is phenyl, substituted phenyl, C₁-C₄alkyl, C₁-C₄alkoxy or —NR₀₈R₀₉;

R₀₈ and R₀₉ independently of one another are C₁-C₄alkyl, phenyl orphenyl which is substituted by halogen, nitro, cyano, C₁-C₄alkyl,C₁-C₄alkoxy, C₁-C₄thioalkyl, —CO₂R₀₆₆, —COR₀₆₇, C₁-C₄alkylsulfonyl,C₁-C₄alkylsulfinyl, C₁-C₄haloalkyl; or R₀₈ and R₀₉ together form a5-6-membered ring which may be interrupted by oxygen, NR₀₆₅ or S,

R₀₁₅, R₀₃₁, R₀₄₃, R₀₄₈, R₀₅₂, R₀₅₆, R₀₆₀ and R₀₆₄ independently of oneanother are hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₃C₆alkynyl orC₃-C₇cycloalkyl;

R₀₂₅, R₀₂₆, R₀₂₇, R₀₂₈, R₀₂₉, R₀₃₀, R₀₃₂, R₀₃₃, R₀₃₄, R₀₃₅, R₀₃₆, R₀₃₇,R₀₄₀, R₀₄₁, R₀₄₂, R₀₄₅, R₀₄₆, R₀₄₇, R₀₄₉, R₀₅₀, R₀₅₃, R₀₅₄, R₀₅₅, R₀₅₇,R₀₅₈, R₀₅₉, R₀₆₁, R₀₆₂, R₀₆₃, R₀₆₅ and R₀₇₀ independently of one anotherare hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇cycloalkyl,phenyl, or phenyl which is substituted by halogen, nitro, cyano,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄ alkylthio, C₁-C₄haloalkylthio,C₁-C₄alkyl or C₁-C₄haloalkyl; and

R₃₆ is C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₃-C₆cycloalkyl or C₃-C₆cycloaikyl whichis substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆alkenyl,C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₄alkoxycarbonyl,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl,C₁-C₄alkylcarbonyl, di-C₁-C₄alkylamino, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O or phenyl which for its partmay be substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆alkenyl,C₃-C₆alkynyl, cyano, nitro or COOH; and agronomically acceptable saltsM⁺ and all stereoisomers and tautomers of the compounds of the formulaI.

The compounds of the formula I can be present in different isomericforms which can be isolated in pure form. The invention therefore alsoembraces all stereoisomeric forms of the compound of the formula I.Examples of these isomeric forms are the formulae Ix, Ixx, Ixxx andIxxxx below, in which Q is the group Q₂.

The alkyl groups occurring in the definitions of the substituents can bestraight-chain or branched and are, for example, methyl, ethyl,n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl,hexyl, heptyl and octyl and their branched isomers. Alkoxy, alkenyl andalkynyl radicals are derived from the alkyl radicals mentioned. Thealkenyl and alkynyl groups can be mono- or polyunsaturated.

Halogen is generally fluorine, chlorine, bromine or iodine. This alsoapplies, correspondingly, to halogen in combination with other meanings,such as haloalkyl or halophenyl.

Haloalkyl groups preferably have a chain length of from 1 to 8 carbonatoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl,1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl,difluoromethyl, trifluoromethyl and dichlorofluoromethyl.

Suitable haloalkenyl groups are alkenyl groups which are mono- orpolysubstituted by halogen, halogen being fluorine, chlorine, bromineand iodine and in particular fluorine and chlorine, for example2,2-difluoro-1-methylvinyl, 3-fluoropropenyl, 3-chloropropenyl,3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl and4,4,4-trifluorobut-2-en-1-yl. Among the C₃-C₂₀alkenyl groups which aremono-, di- or trisubs btuted by halogen, preference is given to thosehaving a chain length of from 3 to 5 carbon atoms.

Suitable haloalkynyl groups are, for example, aikynyl groups which aremono- or polysubstituted by halogen, halogen being bromine, iodine andin particular fluorine and chlorine, for example 3-fluoropropynyl,3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoropropynyl and4,4,4-trifluorobut-2-yn-1-yl. Among the alkynyl groups which are mono-or polysubstituted by halogen, preference is given to those having achain length of from 3 to 5 carbon atoms.

Alkoxy groups preferably have a chain length of from 1 to 6 carbonatoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy,n-butoxy, isobutoxy, sec-butoxy and tert-butoxy and also the isomericpentyloxy and hexyloxy radicals; preferably methoxy and ethoxy.Alkylcarbonyl is preferably acetyl or propionyl. Alkoxycarbonyl is, forexample, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl,isopropoxycarbonyt, n-butoxycarbonyl, isobutoxycarbonyl,sec-butoxycarbonyl or tert-butoxycarbonyl; preferably methoxycarbonyl orethoxycarbonyl. Haloalkoxy groups preferably have a chain length of from1 to 8 carbon atoms. Haloalkoxy is, for example, fluoromethoxy,difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy,1,1,2,2-tetrafluoroethoxy, 24luoroethoxy, 2-chloroethoxy,2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferablydifluoromethoxy, 2-chloroethoxy and trifluoromethoxy. Alkylthio groupspreferably have a chain length of from 1 to 8 carbon atoms. Alkylthiois, for example, methylthio, ethylthio, propylthio, isopropylthio,n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferablymethylthio and ethylthio. Alkylsuffinyl is, for example, methylsulfinyl,ethylsulfinyl, propyisulfinyl, isopropylsulfinyl, n-butylsulfinyl,isobutylsulfiny l, sec-butylsulfinyl, tert-butylsulfinyl; preferablymethylsulfinyl and ethylsulfinyl. Alkylsulfonyl is, for example,methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl,n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl ortert-butylsulfonyl; preferably methylsulfonyl or ethylsulfonyl.Alkoxyalkoxy groups preferably have a chain length of from 1 to 8 carbonatoms. Examples of alkoxyalkoxy groups are: methoxymethoxy,methoxyethoxy, methoxypropoxy, ethoxymethoxy, ethoxyethoxy,propoxymethoxy or butoxybutoxy. Alkylamino is, for example, methylamino,ethylamino, n-propylamino, isopropylamino or the isomeric butylamines.Dialkylamino is, for example, dimethylamino, methylethylamino,diethylamino, n-propylmethylamino, dibutylamino and diisopropylamino.Preference is given to alkylamino groups having a chain length of from 1to 4 carbon atoms. Alkoxyalkyl groups have a chain length of preferablyfrom 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl,methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl,n-propoxyethyl, isopropoxymethyl or isopropoxyethyl. Alkylthioalkylgroups preferably have from 1 to 8 carbon atoms. Alkylthioalkyl is, forexample, methylthiomethyl, methylthioethyl, ethylthiomethyl,ethylthioethyl, n-propylthiomethyl, n-propylthioethyl,isopropylthiomethyl, iso-propylthioethyl, butylthiomethyl,butylthioethyl or butylthiobutyl. The cycloalkyl groups preferably havefrom 3 to 8 ring carbon atoms, for example cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Phenyl, also aspart of a substituent as phenoxy, benzyl, benzyloxy, benzoyl,phenylthio, phenylalkyl, phenoxyalkyl, may be substituted. In this case,the substituents can be in ortho, meta and/or para position. Thepreferred substituent positions are the ortho and para positions to thering attachment point. Heterocyclyl is to be understood as meaning ringsystems which, in addition to carbon atoms, contain at least oneheteroatom, such as nitrogen, oxygen and/or sulfur. They can besaturated or unsaturated. In the context of the present invention,heterocyclyl ring systems may also be substituted. Suitable substituentsare, for example, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, cyano, nitro,C₁-C₄alkylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄alkylthio orC₃-C₆cycloalkyl.

Heterocyclyl may be, for example, furyl, thiophenyl, pyrrolidyl,piperidinyl, morpholinyl, pyridyl, imidazolyl, tetrahydrofuryl,tetrahydropyranyl, dihydrofuryl, dihydropyranyl, isoxazolyl, oxazolyl,isothiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, thiazolyl,pyrazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, tetrazolyl, pyrimidyl,pyrazinyl, sym. or unsym. triazinyl, piperazinyl, oxazolinyl (forexample:

oxazolidinyl, imidazolinyl, imidazolidinyl, dioxanyl, oxetanyl, inparticular 2-oxetanyl, or phthalimidyl.

The invention also embraces the salts M⁺ which can be formed by thecompounds of the formula 1, in particular the compounds of the formula Iin which R₂₀, R₂₃, R₂₆ and R₃₀ are hydroxyl, preferably with amines,alkali metal and alkaline earth metal bases or quaternary ammoniumbases. Among the alkali metal and alkaline earth metal bases, thehydroxides of lithium, sodium, potassium, magnesium or calcium, inparticular those of sodium or potassium, may be especially emphasized assalt formers. Examples of amines suitable for ammonium salt formationare both ammonia and primary, secondary and tertiary C₁-C₁₈alkylamines,C₁-C₄hydroxyalkylamines and C₂-C₄alkoxyalkylamines, for examplemethylamine, ethylamine, n-propylamine, isopropylamine, the fourisomeric butylamines, n-amylamine, isoamylamine, hexylamine,heptylamine, octylamine, nonylamine, decylamine, pentadecylamine,hexadecylamine, heptadecylamine, octadecylamine, methylethylamine,methylisopropylamine, methylhexylamine, methylnonylamine,methylpentadecylamine, methyloctadecylamine, ethylbutylamine,ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine,dimethylamine, diethylamine, di-n-propylamine, diisopropylamine,di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine,diheptylamine, dioctylamine, ethanolamine, n-propanolamine,isopropanolamine, N,N-diethanolamine, N-ethylpropanolamine,N-butylethanolamine, al iylamine, n-butenyl-2-amine, n-pentenyl-2-amine,2,3dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine,propylenediamine, trimethylamine, triethylamine, tri-n-propylamine,triisopropylamine, tri-n-butylamine, triisobutylamine,tri-sec-butylamine, tri-n-amylamine, methoxyethylamine andethoxyethylamine; heterocyclic amiines, for example pyridine, quinoline,isoquinoline, morpholine, piperidine, pyrrolidine, indoline,quinuclidine and azepine: primary arylamines, for example anilines,methoxyanilines, ethoxyanilines, o,m,p-toluidines, phenylenediamines,naphthylamines and o,m,p-chloroanilines; but in particulartriethylamine, isopropylamine and diisopropylamine. Quatemary ammoniumbases which are suitable for salt formation are, for example, [N(R_(a01)R_(b01) R_(c01) R_(d01))]⁺ OH⁻, where R_(a01), R_(b01), R_(c01) andR_(d01) independently of one anotheer are C₁-C₄alkyl. Further suitabletetraalkylammonium bases with other anions can be obtained, for example,by anion exchange reactions.

Preferred compounds of the formula I correspond to the formula Ib

in which

each R independently is C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,C₁-C₆alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkyl,C₁-C₆haloalkylthio, C₁-C₆haloalkylsu ffinyl, C₁-C₆haloalkylsulfonyl,C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkylamino,di-C₁-C₆-alkylamino, C₁-C₆alkylaminosu ffonyl,di-C₁-C₆alkylaminosulfonyl, —N(R₁)—S—R₂, —N(R₃)—SO—R₄, —N(R₅)—SO₂—R₆,nitro, cyano, halogen, hydroxyl, amino, or a five- to ten-memberedmonocyclic or fused bicyclic ring system which may be aromatic orpartially saturated and may contain 1 to 4 heteroatoms selected from thegroup consisting of nitrogen, oxygen and sulfur, where the ring systemis either attached directly to the pyridine ring or attached via aC₁-C₄alkylene group to the pyridine ring, and each ring system may notcontain more than 2 oxygen atoms and not more than two sulfur atoms, andthe ring system for its part may be mono-, di- or trisubstituted byC₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio,C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio,C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₆acetylalkylthio,C₃-C₆alkoxycarbonylalkylthio, C₂-C₄-cyanoalkylthio, C₁-C₆alkylsulfinyl,C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl,C₁-C₃-alkylene-R₇, NR₈R₉, halogen, cyano, nitro, phenyl and benzylthiowhere phenyl and benzylthio for their part may be substituted on thephenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy,halogen, cyano or nitro, and where substituents on the nitrogen in theheterocyclic ring are different from halogen;

Q is the group Q₁ in which

R₂₀ is hydroxyl, C₁-C₄alkoxy, C₁-C₄alkylcarbonyloxy,C₁-C₄alkoxycarbonyloxy, R₂₁R₂₂N—C(O)O, phenylthio, C₁-C₄alky lthio,C₁-C₄alkyl-S(O)₂O, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl(C₁-C₄alkoxy)P(O)O,H(C₁-C₄alkoxy)P(O)O or benzoyloxy; and

R₂₁, and R₂₂ independently of one another are hydrogen or C₁-C₄alkyl; orthe group Q_(2a)

in which R₂₃ is hydroxyl, C₁-C₄alkoxy, C₁-C₄alkylcarbonyloxy,C₁-C₄alkoxycarbonyloxy, R₂₄R₂₅N—C(O)O, phenylthio, C₁-C₄alkylthio,C₁-C₄alkyl-S(O)₂O, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄-alkyl(C₁-C₄alkoxy)P(O)O,H(C₁-C₄alkoxy)P(O)O or benzoyloxy; and

R₂₄ and R₂₅ independently of one another are hydrogen or C₁-C₄alkyl; and

Y is oxygen, sulfur, a chemical bond or a C₁-C₄alkylene bridge;

or the group Q₃

in which R₂₆ is hydroxyl, C₁-C₄alkoxy, C₁-C₄alkylcarbonyloxy,C₁-C₄alkoxycarbonyloxy, R₂₇R₂₈N-C(O)O, phenylthio, C₁-C₄alkylthio,C₁-C₄alkyl-S(O)₂O, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄-alkyl(C₁-C₄alkoxy)P(O)O,H(C₁-C₄alkoxy)P(O)O or benzoyloxy; and

R₂₇ and R₂₈ independently of one another are hydrogen or C₁-C₄alkyl and

R₂₉ is hydrogen, C₁-C₆alkyl, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,(C₁-C₄alkyl)NHCO or (C₁-C₄alkyl)₂NCO; or the group Q₄

in which R₃₀ is hydroxyl, C₁-C₄alkoxy, C₁-C₄alkylcarbonyloxy,C₁-C₄alkoxycarbonyloxy, R₃₁R₃₂N—C(O)O, phenylthio, C₁-C₄alkylthio,C₁-C₄alkyl-S(O)₂O, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄-alkyl(C₁-C₄alkoxy)P(O)O,H(C₁-C₄alkoxy)P(O)O or benzoyloxy; and

R₃₁ and R₃₂ independently of one another are hydrogen or C₁-C₄alkyl;

R₃₃ and R₃₄ independently of one another are hydrogen, C₁-C₄alkyl,C₂-C₆alkenyl, C2-C₆alkynyl, C₁-C₄-alkoxycarbonyl, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₄alkyl-NHS(O)₂,C₁-C₄haloalkyl, —NH—C₁-C₄alkyl, —N(C₁-C₄alkyl)₂, C₁-C₆alkoxy, or phenylwhich for its part may be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₆alkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₄alkyl-S(O)₂O,C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl,C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH,C₁-C₄alkyl-S(O)₂N(C₁-C₄-alkyl), halogen, nitro, COOH or cyano; or R₃₃and R₃₄ together form a C₂-C₆alkylene bridge; and

R₃₅ is hydrogen, C₁-C₄alkyl, C₁-C₄alkoxycarbonyl or phenyl which for itspart may be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino,C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio,C₁-C₄-alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O,C₀-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl,C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH,C₁-C₄alkyl-S(O)₂N(C₁-C₄-alkyl), halogen, nitro, COOH or cyano; or thegroup Q₅, and also agronomically acceptable salts of these compounds,the other substituents being defined as under formula I in claim 1.Among the compounds of the formula lb, preference is furthermore givento those in which the group

—C(O)—Q is located in the 3 position on the pyridine ring, or in which Qis Q₂, R₂₃ being, in particular, hydroxyl, Y being a methylene bridgeand m being the number 2. Preference is further given to compounds ofthe formula lb in which R is C₁-C₆alkyl or C₁-C₆haloalkyl.

Preferred compounds of the formula I are characterized in that the group—C(O)Q is in the ortho position to a group R. Preference is furthermoregiven to compounds of the formula I in which a group R is C₁-C₆haloalkyland in the ortho position to the pyridyl nitrogen. Of particularinterest are furthermore compounds of the formula I in which the group—C(O)Q is in the 3 position to the pyridyl nitrogen. In the formula 1, pis preferably the number 0. Also to be emphasized are compounds of theformula I in which m is 2 and R is C₁-C₃alkyl, C₁-C₃-haloalkyl,C₁-C₂alkoxymethyl, C₁-C₂alkythiomethyl, hydroxymethyl, C₁-C₆alkylcarbonyloxymethyl, benzoyloxymethyl, C₁-C₄alkoxycarbonyloxymethyl,chlorine, cyano, C₁-C₃alkoxy, C₁-C₃haloalkoxy, allyloxy, propargyloxy,C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,C₁-C₃alkylsulfonyloxy, C₁-C₂alkylsulfinylmethyl orC₁-C₂alkylsulfonylmethyl. A further group of preferred compounds of theformula I is formed by those compounds in which at least one group R istrifluoromethyl, difluorochloromethyl, pentafluoroethyl orheptafluoro-n-propyl.

Particularly noteworthy compounds of the formula I are those in which Qis a group Q₁ and R₁₆, R₁₈ and R₁₉ are C₁-C₃alkyl and R₁₇ is hydrogen,or Q is a group Q₂ and Y is —CH₂—, —CH₂CH₂— or oxygen, A is —CH₂— andR₂₄₀, R₂₄₁, R₂₄₂ and R₂₄₃ are Mch hydrogen, or Q is a group Q₃ and R₂₉is C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl or C₁-C₄alkylaminocarbonyl ordi(C₁-C₂-alkyl)aminocarbonyl, or Q is a group Q₄ in which R₃₃, R₃₄ andR₃₅ are C₁-C₃alkyl. In these noteworthy compounds of the formula I, R₂₀,R₂₃, R₂₆ and R₃₀ independently of one another are halogen, thiocyanato,C₁-C₁₂alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₂alkoxy, C₁-C₁₂-alkylthio,alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl,C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl,C₁-C₁₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂alkenylsulfonyl,C₂-C₁₂-haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl,C₂-C₁₂haloalkenylsulfonyl, C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl,C₂-C₁₂alkynylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₂-alkylthio,C₁-C₄-alkoxycarbonyl-C₁-C₂alkylsulfinyl,C₁-C₄alkoxycarbonyl-C₁-C₂alkylsulfonyl, C₁-C₄alkyl-S(O)₂NH,C₁-C₄haloalkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy,C₂-C₁₈-alkenylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy,C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂-alkylthiocarbonyloxy,C₁-C₁₂alkylthiocarbamoyl, C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)—NH—,di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)—NH—, benzyloxy, benzylthio,benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl,phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groupsfor their part may in each case be substituted by C₁-C₄alkyl,C₁-C₄-haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl,C₁-C₄alkoxycarbonyl, C₁-C₄-alkylamino, di-C₁-C₄alkylamino,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsuonyl,C₁-C₄-alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl,C₁-C₄haloalky lsulfonyl, C₁-C₄-haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH,C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano, or R₂₀, R₂₃, R₂₆and R₃₀ independently of one another are thienylcarbonyloxy orfurylcarbonyloxy which for their part may be substituted by methyl orhalogen, or are pyridylcarbonyloxy which for its part may be substitutedas stated in claim 1, or R₂₀ is R₃₇R₃₇N, R₇₁R₇₂NNH—, R₂₁R₂₂NC(O)O— orR₇₃R₇₄NC(O)NH—; or R₂₃ is R₄₄R₄₅N, R₇₅R₇₆NNH—, R₄₆R₄₇NC(O)O— orR₇₇R₇₈NC(O)NH—; or R₂₆ is R₅₃R₅₄N, R₇₉R₈₀NNH—, R₅₅R₅₆NC(O)O— orR₈₁R₈₂NC(O)NH—; or R₃₀ is R₆₂R₆₃N, R₈₃R₈₄NNH—, R₆₄R₆₅NC(O)O— orR₈₅R₈₆NC(O)NH—. Very particularly preferably, R₂₀, R₂₃, R₂₆ or R₃₀ arehydroxyl or O⁻M⁺.

A further preferred group is formed by those compounds of the formula Iin which Q is a group Q₅, R₃₆ is C₁-C₄alkyl, C₁-C₄haloalkyl orcyclopropyl and R₀₁ is C₁-C₆alkyl, C₁-C₄-alkoxycarbonylmethyl,C₃-C₈alkenyl, is benzyl or phenyl substituted by methyl, halogen,trifluoromethyl, methoxy, and at least one group R is trifluoromethyl,difluorochloromethyl, pentafluoroethyl or heptafluoro-n-propyl locatedin the ortho position to the pyridyl nitrogen.

The process according to the invention for preparing compounds of theformula I

in which R and m are as defined under formula 1; p is 0 and Q is thegroup

is carried out analogous ly to known processes (for example thosedescribed in WO 97/46530 and EP-A-0 353 187) and comprises

a) reacting a compound of the formula II

 in which R and m are as defined under formula I and X is a leavinggroup, for example halogen, in an inert organic solvent in the presenceof a base with compounds of the formula III, IV,V or VI

 in which R₁₆, R₁₇, R₁₈, R₁₉,R₂₉, R₃₃, R₃₄, R₃₅, R₂₄₀, R₂₄₃, R₂₄₂, R₂₄₁,A and Y are as defined under formula I to give the compounds of theformula VII, VIII, IX or X

 and then isomerizing these compounds, for example in the presence of abase and a catalytic amount of dimethylaminopyridine (DMAP) or a sourceof cyanide; or

b) reacting a compound of the formula XI

 in which R and m are as defined under formula I with compounds of theformula III, IV, V or VI

 in which R₁₆, R₁₇, R₁₈, R₁₉, R₂₉, R₃₃, R₃₄, R₃₅, R₂₄₀, R₂₄₃, R₂₄₂,R₂₄₁, A and Y are as defined under formula I in an inert organic solventin the presence of a base and a coupling agent to give a compound of theformula VII, VIII, IX or X

 and then isomerizing these compounds, for example as described underroute a).

Compounds of the formula I in which R₂₀, R₂₃, R₂₆ and R₃₀ are differentfrom hydroxyl or halogen can be prepared by converesion methods whichare generally known from the literature, for example acyclations orcarbamoylations with appropriate acyl chlorides, from compounds in whichR₂₀, R₂₃, R₂₆ or R₃₀ is hydroxyl in the presence of a suitable base, orthey can be prepared by nucleophilic substitution reactions on chloridesof the formula I in which R₂₀, R₂₃, R₂₆ or R₃₀ is halogen, which arelikewise obtainable by known processes by reaction with a chlorinatingagent, such as phosgene, thionyl chloride or oxalyl chloride. Here, forexample, suitably substituted amines, or hydroxylamines directly, oralkylsulfonamides, mercaptans, thiophenols, phenols, Ar₁—NH₂ or Ar₁—SH,are employed in the presence of a base, for example5-ethyl-2-methylpyridine, diisopropylethylamine, triethylamine, sodiumbicarbonate, sodium acetate or potassium carbonate.

Compounds of the formula I in which R₂₀, R₂₃, R₂₆ or R₃₀ comprise thiogroups can be oxidized analogously to known standard processes, forexample using peracids, for example meta-chloroperbenzoic acid (m-CPBA)or peracetic acid, to give the corresponding sulfones and sulfoxides ofthe formula I. Here, the degree of oxidation at the sulfur atom (SO— orSO₂—) can be controlled by the amount of oxidizing agent.

The process according to the invention for preparing compounds of theformula I in which R and m are as defined under formula I and Q is agroup

in which Z is sulfur, q is 0 and R₃₆ and R₀₁ are as defined underformula I is carried out analogously to known processes (for examplethose described in WO 97/43270) and comprises converting a compound ofthe formula XII

in which R₃₆, R and m are as defined under formula I in the presence ofa base, carbon disulfide and an alkylating agent of the formula XIII

R₀₁—X₁  (XIII),

in which R₀₁ is as defined under formula I and X₁ is a leaving group,for example halogen or sulfonate, into the compound of the formula XIV

in which Z is sulfur and R, R₀₁, R₃₆ and m are as defined above and thencyclizing this compound using hydroxylamine hydrochloride, in thepresence or absence of a solvent, in the presence of a base to give thecompounds of the formulae

in which Z is sulfur and R, R₃₆, R₀₁ and m are as defined above, andthen oxidizing these compounds with an oxidizing agent, for examplemeta-chloroperbenzoic acid (m-CPBA). The isomers of the formulae le andIf can be separated using column chromatography and a suitable mobilephase and then purified.

The preparation of the compounds of the formula I in which p is 0 isillustrated in more detail in the reaction schemes 1 and 2 below.

According to this reaction scheme, the compounds of the formula I withthe group Q₁ in which R₂₀ is hydroxyl, the compounds of the formula Iwith the group Q₂ in which R₂₃ is hydroxyl, the compounds of the formulaI with the group Q₃ in which R₂₆ is hydroxyl and the compounds of theformula I with the group Q₄ in which R₃₀ is hydroxyl can preferably beprepared.

For preparing the compounds of the formula I in which Q is the groups Q₁to Q₄ and R₂₀, R₂₃,R₂₆ and R₃₀ are hydroxyl, in accordance with reactionscheme 1, route a), the carboxylic acid derivatives of the formula II inwhich X is a leaving group, for example halogen, for example iodine,bromine and in particular chlorine, N-oxyphthali r nide or N,O—dimethylhydroxylamino or part of an activated ester, for example

(formed from dicyclohexylcarbodiimide (DCC) and the correspondingcarboxylic acid) or

(formed from N-ethyl-N′-(3-dimethyiaminopropyl)carbodiimide (EDC) andthe corresponding carboxylic acid) are employed. These compounds arereacted in an inert organic solvent, for example a halogenatedhydrocarbon, for example dichloromethane, a nitrile, for exampleacetonitrile, or an aromatic hydrocarbon, for example toluene, and inthe presence of a base, for example an alkylamine, for exampletriethylamine, an aromatic amine, for example pyridine or4-dimethyiaminopyridine (DMAP), with the dione derivatives of theformula III, IV, V or VI to give the isomeric enol ethers of theformulae VII, VIII, IX and X. This esterification is carried out attemperatures of from 0° C. to 110° C.

The isomerization of the ester derivatives of the formulae VII, VIII, IXand X to the dione derivatives of the formula I (in which R₂₀, R₂₃, R₂₆and R₃₀ are hydroxyl) can be carried out, for example, analogously to EP369 803 in the presence of a base, for example an alkylamine, forexample triethylamine, a carbonate, for example potassium carbonate, anda catalytic amount of DMAP or a cyanide source, for example acetonecyanohydrin or potassium cyanide.

According to reaction scheme 1, route b), the desired diones of theformula I (in which R₂₀, R₂₃, R₂₆ and R₃₀ are hydroxyl) can be obtained,for example, in analogy to Chem. Lett. 1975, 1045 by esterifying thecarboxylic acids of the formula Xl with the dione derivatives of theformula III, IV, V or VI in an inert solvent, for example a halogenatedhydrocarbon, for example dichloromethane, a nitrile, for exampleacetonitrile, or an aromatic hydrocarbon, for example toluene, in thepresence of a base, for example an alkylamine, for exampletriethylamine, and a coupling agent, for example2-chloro-1-methylpyridinium iodide. Depending on the solvent used, thisesterification is carried out at temperatures of from 0° C. to 110° C.,affording initially, as described under route a), the isomeric ester ofthe formula I which can be isomerized as described under route a), forexample in the presence of a base and a catalytic amount of DMAP, or acyanide source, to give the desired dione derivative of the formula I(R₂₀, R₂₃, R₂₆ and R₃₀ are hydroxyl).

The preparation of the compounds of the formula I in which Q is thegroup Q₅ can be carried out in accordance with reaction scheme 2 byreacting the β-diketone derivative of the formula XII, for example inanalogy to Synthesis 1991, 301; ibid. 1988, 793; or Tetrahedron 32, 3055(1976) with carbon disulfide in the presence of a base, for example acarbonate, for example potassium carbonate, a metal hydride, for examplesodium hydride, or potassium fluoride on aluminium, and an alkylatingagent of the formula XIII in which X₁ is a leaving group, for examplehalogen, for example iodine, bromine and in particular chlorine,

This reaction is preferably carried out in the presence of a solvent,for example an amide, for example N,N-dimethylformamide (DMF), asulfoxide, for example dimethylsulfoxide (DMSO), or a nit rle, forexample acetonitrile. The ketene thioacetal of the formula XIV which isformed is cyclized with the aid of hydroxylamine hydrochloride in thepresence of a base, for example sodium acetate, in a solvent, forexample an alcohol, for example ethanol, or an ether, for exampletetrahydrofuran, to give the compound of the formula le in which Z issulfur. This cyclization reaction is carried out at temperatures of from0° C. to 100° C. If appropriate, compounds of the formulae le and If (Zis sulfur) can be oxidized analogously to known standard processes, forexample with peracids, for example meta-chloroperbenzoic acid (m-CPBA)or peracetic acid, to give the corresponding sulfones and sulfoxides ofthe formulae Ie and If (Z═SO— or SO₂—). Here, the degree of oxidation atthe sulfur atom (Z═SO— or SO_(2—)) can be controlled by the amount ofoxidizing agent.

Oxidations to the compounds of the formulae le and If (Z is SO— orSO_(2—)) are carried out as described, for example, in H.O. House,“Modern Synthetic Reactions” W. A. Benjamin, Inc., Menlo Park, Calif.,1972, pages 334-335 and 353-354.

The activated carboxylic acid derivatives of the formula II in reactionscheme 1 (route a) in which X is a leaving group, for example halogen,for example bromine, iodine or in particular chlorine, can be preparedby known standard processes, as described, for example, in C. Ferri“Reaktionen der organischen Synthese” [Reactions of Organic Synthesis],Georg Thieme Verlag, Stuttgart, 1978, page 461 ff. This is shown inreaction scheme 3 below.

According to reaction scheme 3, the compounds of the formula II(X=leaving group) or II (X=halogen) are prepared, for example, byemploying a halogenating agent, for example a thionyl halide, forexample thionyl chloride or thionyl bromide; a phosphorus halide orphosphorus oxyhalide, for example phosphorus pentachloride or phosphorusoxychloride or phosphorus pentabromide or phosphoryl bromide; or anoxalyl halide, for example oxalyl chloride, or by employing a reagentfor the formation of activated esters, for exampleN,N′-dicyclohexylcarbodiimide (DCC) orN-ethyl-N′-(3-dimethylaminopropyli)carbodiimide (EDC) of the formula X.For the compound of the formula X used as halogenating agents, X is aleaving group, for example halogen, for example fluorine, bromine oriodine and in particular chlorine, and W₁ is, for example, PCI₂, SOCI,SOBr or CICOCO. The reaction is carried out in the presence or absenceof an inert organic solvent, for example in aliphatic, halogenatedaliphatic, aromatic or halogenated aromatic hydrocarbons, for examplen-hexane, benzene, toluene, xylenes, dichloromethane, 1,2-dichloroethaneor chiorobenzene, at reaction temperatures in the range of from −20° C.to the reflux temperature of the reaction mixture, preferably at 40-150°C., and in the presence of a catalytic amount of N,N-dimethylformamide.Such reactions are generally known and described in the literature invarious variations with respect to the leaving group X.

The compounds of the formulae III, IV, V and VI are known and can beprepared analogously to the methods described, for example, in WO92/07837, DE-A-3818958, EP-A-0 338 992 and DE-A-3902818.

The compounds of the formula XII in reaction scheme 2 can be obtained bystandard processes, for example from the corresponding compounds of theformula II

in which R and m are as defined above and X is a leaving group, forexample halogen, for example via Claisen condensation, or from thecompounds of the formula II by reaction with a ketocarboxylic acid saltof the formula XV

in which R₃₆ is as defined under formula I and M⁺ is an alkali metal ion(cf., for example, WO 96/26192).

The compounds of the formulae II and XI are known and can be preparedanalogously to the methods described, for example, in WO 97146530,EP-A-0 353 187, Heterocycles, 48, 779 (1998), Heterocycles, 46, 129(1997), or Tetrahedron Letters, 1749 (1998).

For preparing all other compounds of the formula I functionalizedaccording to the definition of (R)_(m), there is a large number of knownstandard processes available, for example alkylation, halogenation,acylation, amidation, oximation, oxidation and reduction, and the choiceof the suitable preparation processes depends on the properties(reactivities) of the substituents in the intermediates in question.

All further compounds originating from the scope of the formula I can beprepared in a simple manner, taking into account the chemical propertiesof the pyridyl or Q moiety.

The end products of the formula I can be isolated in a customary mannerby concentration or evaporation of the solvent and be purified byrecrystallization or trituration of the solid residue in solvents inwhich they are only sparingly soluble, such as ethers, aromatichydrocarbons or chlorinated hydrocarbons, by distillation or by means ofcolumn chromatography and a suitable mobile phase.

Furthermore, it is known to the person skilled in the art in which ordercertain reactions have to be carried out advantageously to avoidpossible side reactions. Unless a targeted synthesis is carried out forisolating pure isomers, the product may be obtained as a mixture of twoor more isomers. The isomers can be separated by methods known per se.

Compounds of the formula I in which p is 1, i.e. the correspondingN-oxides of the formula I, can be prepared by reacting a compound of theformula I in which p is 0 with a suitable oxidizing agent, for examplewith the H₂O₂ urea adduct, in the presence of an acid anhydride, forexample trifluoroacetic anhydride. This reaction sequence isdemonstrated using the example of group Q₂ below:

Compounds of the formula I in which R in the ortho position to thepyridine nitrogen is 1-chloro-C₁-C₂alkyl, 1-hydroxy-C₁-C₂alkyl,1-(C₁-C₆alkylcarbonyloxy)-C₁-C₂alkyl, 1 -benzoyloxy-C₁-C₂alkyl,1-(C₁-C₄alkoxycarbonyloxy)-C₁-C₂alkyl, 1-(C₁-C₄alkylthio)-C₁-C₂alkyl,1-(C₁-C₄-alkylsulfinyl)-C₁-C₂alkyl, 1-(C₇-C₄alkylsulfonyl)-C₁-C₂alkyl,1-thiocyanato-C₁-C₂alkyl, 1-cyano-C₁-C₂alkyl, can also be prepared, forexample, by heating an N-oxide of the formula I under known reactionconditions, for example in the presence of tosyl chloride (see, forexample, Parham, W. E.; Sloan, K. B.; Reddy, K. R.; Olson, P. E.; J OrgChem 1973, 38, 927) or in the presence of an acid anhydride (see, forexample, Konno, K.; Hashimoto, K.; Shirahama, H.; Matsumoto, T.;Heterocycles 1986, 24, 2169), followed, if appropriate, by subsequentconversion.

The compounds of the formula XXIIa are synthesized analogously to knownprocesses, for example those mentioned in Heterocycles, 46, 129 (1997)or Helvetica Chimica Acta 71, 596 (1988), and comprises either

a) acylating a compound of the formula XVI

in which R₃₀₁ is hydrogen or C₁-C₆alkyl;

R₄₀₁ is hydrogen, C₁-C₆alkyl C₂-C₆alkenyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy,C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkyl,1-(C₁-C₆alkylcarbonyloxy)-C₁-C₆alkyl, 1-(C₁-C₆alkylthio)-C₁-C₆-alkyl,1-(C₁-C₆alkylsulfinyl)-C₁-C₆alkyl, 1-(C₁-C₆alkylsulfonyl)-C₁-C₆alkyl,1-thiocyanato-C₁-C₆-alkyl, 1-cyano-C₁-C₆alkyl, phenyl, where the phenylgroups may be mono- or polysubstituted by halogen, methyl, ethyl,trifluoromethyl, methoxy or nitro, or is a five- to ten-memberedmonocyclic or fused bicyclic ring system which may be aromatic orpartially saturated and may contain 1 to 4 heteroatoms selected from thegroup consisting of nitrogen, oxygen and sulfur, where the ring systemis either attached directly or via a C₁-C₄alkylene group to the doublebond, and each ring system may not contain more than 2 oxygen atoms andnot more than two sulfur atoms and the ring system for its part may bemono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy,mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio,C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio,C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio,C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl,C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₈₇, NR₈₈R₈₉, halogen, cyano,nitro, phenyl and benzylthio, where phenyl and benzylthio for their partmay be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃-haloalkoxy, halogen, cyano or nitro and wheresubstituents on nitrogen in the heterocyclic ring are different fromhalogen;

R₈₇ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for itspart may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃-alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro;

R₈₈ is hydrogen or C₁-C₆alkyl and

R₈₉ is C₁-C₆alkyl or C₁-C₆alkoxy;

with a compound of the formula XVII

in which R₅₀₁ is C₁-C₆haloalkyl and X₂ is O(CO)R₅₀₁ or halogen to givethe compound of the formula XVIII

in which R₃₀₁, R₄₀₁, R₅₀₁, and R₁₄ are as defined above, in the presenceof a base, for example an aromatic amine, for example pyridine, andsubsequently replacing the alkoxy group by the amino group using ammoniain an organic solvent, for example a halogenated hydrocarbon, forexample dichloromethane, or a nitrile, for example acetonitrile. Theresulting compound of the formula XIX

is subsequently condensed with a compound of the formula XX

in which R₂₀₁ is C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl,C₂-C₆alkynyl, C₂-C₆-haloalkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,1-(C₁-C₆alkylcarbonyloxy)-C₁-C₆alkyl, 1-(C₁-C₆alkylthio)-C₁-C₆alkyl,1-(C₁-C₆alkylsulfinyl)-C₁-C₆alkyl, 1-(C₁-C₆alkylsulfonyl)C₁-C₆alkyl,1-thiocyanato-C₁-C₆alkyl, 1-cyano-C₁-C₆alkyl, C₁-C₆alkoxy-C₁-C₆alkyl,C₁-C₆alkoxycarbonyl-C₁-C₆alkoxy, C₁-C₆alkylthio-C₁-C₆alkoxy, phenyl,benzyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, benzyithio,benzylsulfinyl or benzylsulfonyl, where the phenyl groups may be mono-or polysubstituted at least by halogen, methyl, ethyl, trifluoromethyl,methoxy or nitro, or is a five- to ten-membered monocyclic or fusedbicyclic ring system which may be aromatic or partially saturated andmay contain 1 to 4 heteroatoms selected from the group consisting ofnitrogen, oxygen and sulfur, where the ring system is attached eitherdirectly or via a C₁-C₄-alkylene group and each ring system may notcontain more than 2 oxygen atoms and not more than two sulfur atoms, andthe ring system for its part may be mono-, di- or trisubstituted byC₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆a lkoxy, C₁-C₆haloalkoxy,C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio,C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio,C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio,C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl,C₁-C₆haloalky lsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl,aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl,C₁-C₃-R₉₀, NR₉₁R₉₂, halogen, cyano, nitro, phenyl and benzylthio, wherephenyl and benzylthio for their part may be substituted on the phenylring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃-haloalkoxy,halogen, cyano or nitro, and where substituents on nitrogen in theheterocyclic ring are different from halogen;

R₉₀ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio,C₁-C₃alkylsuffinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for itspart may be substituted by C₁-C₃-alkyl, C₁-C₃haloalkyl, C₁-C₃-alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro;

R₉₁ is hydrogen or C₁-C₆alkyl and

R₉₂ is C₁-C₆alkyl or C₁-C₆alkoxy and

R₁₄ is as defined above, and the resulting compound of the formula XXIa

 is subsequently hydrolysed to give the compound of the formula XXIIa

 in which R₂₀₁, R₃₀₁, R₄₀₁, and R₅₀₁ are as defined above, or

b) condensing a compound of the formula XXIII

 in which R₁₄ is as defined above with a compound of the formula XXIV

 and chlorinating the resulting compound of the formula XXV

 in which R₃₀₁, R₄₀₁ and R₅₀₁ are as defined above and R₁₄ is C₁-C₄alkylto give compounds of the formula XXVI

 in which R₃₀₁, R₄₀₁, R₅₀₁ and R₁₄ are as defined above (using, forexample, POCI₃), and subsequently reacting this compound with anucleophile of the formula XXVII

Z—R₁₅₀  (XXVII)

In which Z is SH, OH or amino and R₁₅₀ is C₁-C₆alkyl, C₃-C₆alkeny4C₃-C₆halogenalkenyl, C₃C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkyl, phenyl, benzyl, where the phenyl and benzyl groups fortheir part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, isC₁-C₁alkoxy-C₁-C₄alkyl or C₁-C₄-alkylthio-C₁-C₄alkyl,C₁-C₄alkylsulfinyl-C₁-C₄alkyl, C₁-C₄alkylsulfonyl-C₁-C₄alkyl, or a five-to ten-membered monocyclic or fused bicyclic ring system which may bearomatic or partially saturated and may contain 1 to 4 heteroatomsselected from the group consisting of nitrogen, oxygen and sulfur, andeach ring system may not contain more than 2 oxygen atoms and not morethan two sulfur atoms, and the ring system for its part may be mono-,di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl,C₃-C₆haloalkenyl, C₃-C₆-alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto,C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio,C₃-C₆haloalkenylthio, C₃-C₆-alkynylthio, C₂-C₅alkoxyalkylthio,C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio,C₂-C₄-cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl,C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃-alkylene-R₉₃,NR₉₄R₉₅, halogen, cyano, nitro, phenyl and benzylthio, where phenyl andbenzylthio for their part may be substituted on the phenyl ring byC₁-C₃alkyl, C₁-C₃-haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen,cyano or nitro, and where substituents on nitrogen in the heterocyclicring are different from halogen;

R₉₃ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for itspart may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro;

R₉₄ is hydrogen or C₁-C₆alkyl and

R₉₅ is C₁-C₆alkyl or C₁-C₆alkoxy;

in the presence of a base to give compounds of the formula XXIb

in which R₁₄, R₁₅₀, R₃₀₁, R₄₀₁, and R₅₀₁ are as defined above, andsubsequen tly hydrolysing the resulting compound to give the compound ofthe formula XXIIb

in which R₁₅₀, R₃₀₁, R₄₀₁ and R₅₀₁ are as defined.

Compounds of the formula XXIb in which R₁₅₀ is fluorine are prepared byreacting a compound of the formula XXVI in the presence of a polaraprotic solvent, for example acetonitrile, dimethylformamide orsulfolane, with potassium fluoride in the presence or absence of acatalytic amount of 18-crown-6. Compounds of the formula XXIc in whichR₁₅₀ is hydrogen are preparerd by reducing the chlorine group in theformula XXVI, for example using hydrogen in the presence of a suitablemetal catalyst or using ammonium formate in a suitable solvent. Thepreparation of the compounds of the formula XXIIa, or XXIIb and XXIIc isillustrated in more detail in the reaction schemes 4 and 5 below.

For preparing all other compounds of the formula I which arefunctionalized according to the definition of R₂₀₁ (R₁₅₀) to R₅₀₁, alarge number of known standard processes is suitable, for examplealkylation, halogenation, acylation, amidation, oximation, oxidation andreduction, the choice of the suitable preparation processes depending onthe properties (reactivities) of the substituents in the intermediatesin question.

The novel compounds of the formula IIb in which R_(f) istrifluoromethyl, difluorochloromethyl, pentafluoroethyl,heptafluoro-n-propyl or trichloromethyl, R_(X1) is C₁-C₆alkyl and Q andR are as defined under formula I can be prepared by generally knownprocesses via 3-alkoxycarbonyl-4-perhaloalkylpyridine N-oxides of theformula XXVIII according to reaction scheme 5 by preparing, usingsuitable chlorination conditions and separation processes, the6-chloro-4-haloalkyl-3-nicotinic esters of the formula XXX and thenconverting these compounds with a nucleophile of the formula XXXI

Z₀₁—R_(151tm (XXXI))

in which Z₀₇ is SH, hydroxyl, halogen or amino and R₁₅₁ is hydrogen,C₁-C₆alkyl, C₃-C₆-alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, halogen,C₃-C₆haloalkynyl, C₁-C₆alkylsulfonyl, C₁-C₆-haloalkyl, phenyl, benzyl,where the phenyl and benzyl groups for their part may be substituted byC₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyanoor nitro, is C₁-C₄alkoxy-C₁-C₄alkyl or C₁-C₄alkylthio-C₁-C₄alkyl ,C₁-C₄alkylsulfinyl-C₁-C₄alkyl, C₁-C₄alkylsulfonyl-C₁-C₄alkyl, or a five-to ten-membered monocyclic or fused bicyclic ring system which may bearomatic or partially saturated and may contain 1 to 4 heteroatomsselected from the group consisting of nitrogen, oxygen and sulfur, andeach ring system may not contain more than 2 oxygen atoms and not morethan two sulfur atoms, and the ring system for its part may be mono-,di- or trisubstituted by

C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆-haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio,C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio,C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio,C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio,C_(l)-C₆-alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl,C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R_(96,) NR97R₉₈, halogen,cyano, nitro, phenyl or benzylthio, where phenyl and benzylthio fortheir part may be substituted on the phenyl ring by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃-haloalkoxy, halogen, cyano or nitro,

R₉₆ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for itspart may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃-alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro;

R₉₇ is hydrogen or C₁-C₆alkyl and

R₉₈ is C₁-C₆alkyl or C₁-C₆alkoxy;

and where substituents on nitrogen in the heterocyclic ring aredifferent from halogen, using reaction processses which are generallyknown to the person skilled in the art, into the 6-substituted4-perhaloalkylnicotinic acids of the formula XXXII and their subsequentproducts of the formulae IIb and Ib as described in reaction scheme 1.This is shown in reaction scheme 6 below.

According to this reaction scheme, it is preferably possible to preparethe compounds of the formula I with the group Q₁ in which R₂₀ ishydroxyl, the compounds of the formula I with the group 02 in which R₂₃is hydroxyl, the compounds of the formula I with the group Q₃ in whichR₂₆ is hydroxyl and the compounds of the formula I with the group Q₄ inwhich R₃₀ is hydroxyl.

6-substituted 2-haloalkylnicotinic acid compounds of the formula Ic canbe prepared, for example, from the corresponding2-haloalkyl-3-alkoxycarbonyl-2-pyridines XXXIII in which R_(f) istrifluoromethyl, difluorochloromethyl, pentafluoroethyl,heptafluoro-n-propyl or trichioromethyl and R_(1x) is C₁-C₆alkyl and Ris as defined under formula I, by hydrolysis into the correspondingcarboxylic acids and their subsequent activation, for example byconversion into an acylhalide (IIc). (Reaction scheme 7).

Their precursors of the formulae XXXIIIa, XXXIIIb, XXXIIIc, XXXIIId,XXXIIIe, XXXIIIf, XXXIIIg and XXXIIIh are likewise accessible byconversion processes known to the person skilled in the art (reactionshceme 7). 2-Trifluoromethyl-3-ethoxycarbonyl-2-pyridone (formulaXXXIIIa in which R is hydrogen, R_(1X) is ethyl and Rf istrifluoromethyl) in particular is known form Org. Process Research &Developmnet, 1, 370 (1997).

Intermediates of the formulae XXXIIIa to XXXIIIh can be obtained byreacting, for example for preparing a 6-halo derivative of the formulaXXXIIId, a pyridone of the formula XXXIIIa (preparation according toOrg. Process Research & Development, 1, 370 (1997) or scheme 8) with ahalogenating agent, for example phosphorus oxychloride, phosphorusoxybromide or phenyl dichlorophosphate, in the presence or absence ofadded base, such as a dialkylaniline, in the presence or absence ofsolvent, if desired in a pressure vessel, at temperatures between 0 and220° C. (preferably 60-200° C.). It is known to the person skilled inthe art how to convert chloro derivatives by nucleophilic substitution,for example using an alkali metal iodide in an inert solvent into thecorresponding iodides, or using gaseous hydrobromic acid in lowercarboxylic acids, for example conc. acetic acid, into the correspondingbromo derivatives (for example according to U.S. Pat. No. 3,974,166) orusing alkali metal fluoride in a dipolar solvent, such as sulfolane,into the corresponding fluoro derivatives.

The compound of the formula XXXIIIe can be prepared by reacting a haloderivative of the formula XXXIIId obtained as described above with analcohol of the formula R₁₅₁—OH in the presence of a base, such as sodiumhydride, or an alkali metal oxide or carbonate, or directly with analkali metal alkoxide, in an inert solvent such as dimethylformamide orin an excess of the alcohol of the formula R₁₅₁—OH which corresponds tothe group to be introduced, at temperatures between −5 and 160° C., orby reacting, to prepare a corresponding 6-thioether of the formulaXXXIIIc, analogously to what was described above, either the halide ofthe formula XXXIIId with a thiol of the formula R₁₅₁—SH in the presenceof a base such as sodium hydride or with an alkali metal salt of a thiolin an inert solvent at −10-150° C., or by preparing, starting from apyridone XXXIIIa and using a thionating agent, for example Lawesson'sreagent, in an inert solvent, such as toluene or acetonitrile, apyrithione of the formula XXXIIIb and alkylating this with an alkylatingagent R₁₅₁-X, where X is a leaving group, such as halide (Cl, Br, I) orROSO₃— or RSO₂—, at 20-120° C. in an inert solvent, such astetrahydrofuran, to give the thioether of the formula XXXIIIc, or, toprepare the corresponding sulfinyl or sulfonyl derivative of the formulaXXXIIIf, reacting with an oxidizing agent, such as m-chloroperbenzoicacid or sodium periodate, or sodium perborate, under temperature controlknown to the person skilled in the art, depending on the degree ofoxidation (for example −30° C.-+50° C. for m₀₁=1 or −20° C.-+100° C. form₀₁=2) in an inert solvent, such as dichloromethane, to give XXXIIIf,or, to prepare 6-alkyl derivatives XXXIIIg according to the invention,reacting a sulfone of the formula XXXIIIf (m₀₁=2) or a halo derivativeof the formula XXXIIId in the presence or absence of a Pd(O) catalystsuch as Pd(PPh₃)₂Cl₂ with a tetra-C₁-C₆alkyltin or with a Grignardreagent C₁-C₆alkyl-MgHal at temperatures between −10° and 180° C., forexample analogously to Synlett 1998 (1185), or as described inOrganocopper Reagents, R. J. K. Taylor, Oxford University Press 1994, orin Transition Metals in Organic Synthesis, S. Gibson, Oxford Univ.Press,1997, or in Org. React. 50, 1 (Stille reaction), or, to prepare6-cyano derivatives of the formula XXXIIIh, reacting a halide of theformula XXXIIId or a sulfone of the formula XXXIIIf (m₀₁=2) with analkali metal or tetraalkylammonium cyanide or copper cyanide in an inertsolvent, such as dichloromethane, tetrahydrofuran or dimethylformamide,at temperatures between 0° C. and 220° C.

Some of the compounds of the formula XXXIIIe are also obtainable fromthe pyridone of the formula XXXIIIa by reacting them analogously to Org.React. 42, 2 with an alcohol R₁₅₁OH in the presence of anazodicarboxylic ester (for example diethyl ester) and triphenylphosphinein an inert solvent, such as tetrahydrofuran or dioxane. (Scheme 9)

The intermediates of the formula XXXIIIa required in reaction scheme 8as starting materials are obtainable according to Scheme 10 route A orroute B (Org. Process Research & Development, 1, 370 (1997)) or route C.

Intermediates of the formula XXXIIIa are obtainable by route A byreacting, to prepare the3,4-dihydro-5-alkoxycarbonyl-6-haloalkylpyridin-2-ones of the formulaXXXVIII, an enamine of the formula XXXV in the presence or, preferably,in the absence of a solvent either in an excess of enamine or in thepresence of a base, such as a tert-amine, with an acryloyl chloride ofthe formula XXXIV at temperatures between −10° and +200° C., or byreacting a keto ester of the formula XXXVII with an acrylamide of theformula XXXVI in the presence of a catalyst such as p-toluenesulfonicacid (=HOTs) in an inert solvent, such as toluene, at temperaturesbetween 30 and 200° C., with removal of the water of reaction formed(for example azeotropic distillation), or by reacting a keto ester ofthe formula XXXVII in the presence of a base, such as an alkali metalalkoxide or magnesium alkoxide, with a 4-haloketo ester of the formulaXXXIX in an inert solvent, such as ethanol, at 0-180° C. to give theintermediate of the formula XXXX, converting this with ammonia or anammonium salt, such as ammonium acetate, or with a bis-silylamine suchas hexamethyldisilazane, in the presence or absence of an acidiccatalyst, such as sulfuric acid or p-toluenesulfonic acid or an organiccarboxylic acid (for example conc. acetic acid), in an inert solvent andat temperatures between 0° and 180° C. into the corresponding enamine ofthe formula XXXXI, subsequently cyclizing in the presence of a catalyst,such as p-toluenesulfonic acid or sulfuric acid, if desired withcontinuous removal of the water of reaction formed in an inert solvent,such as toluene, to give the dihydropyridone of the formula XXXVIII, andfinally treating with an oxidizing agent, such as manganese dioxide, inan inert solvent, such as chlorobenzene, at temperatures between 50 and250° C., to prepare the pyridones XXXIIIa.

The intermediates of the formula IIa

in which Q_(a) is hydroxyl, halogen, cyano, or a group —CH₂(CO)R₃₆ or

R_(b) is hydrogen, C₁-C₄alkyl or halogen;

R₁ is trifluoromethyl, difluorochloromethyl, pentafluoroethyl,heptafluoro-n-propyl or trichloromethyl;

R_(a) is C₁-C₃alkyl, C₁-C₃haloalkyl, C₃-C₄cycloalkyl,C₁-C₂alkoxy-C₁-C₄alkyl, C₁-C₂-alkylthiomethyl, hydroxyl, halogen, cyano,C₁-C₃alkoxy, C₁-C₃haloalkoxy, allyloxy, propargyioxy, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or C₁-C₃alkylsulfonyloxy, and R₀₁and R₃₆ are as defined under group O₅ of the formula 1, except for thecompounds 2,6-bistrifluoromethyinicotinic acid,2,6-bistrifluoromethyl-5-methoxynicotinic acid and2-hydroxy-6-trifluoromethyinicotinic acid, are novel and thereforelikewise form part of the subject matter of the present invention.

Compounds of the formula IIb

in which Q_(b) is hydroxyl, halogen, cyano or a group —CH₂(CO)R₉₉ or

R₉₉ is C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₄cycloalkyl or C₁-C₄alkoxy;

R_(f) is trifluoromethyl, difluorochloromethyl, pentafluoroethyl orheptafluoro-n-propyl; and

R_(c) is C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₂alkoxymethyl,C₁-C₁alkylthiomethyl, hydroxyl, halogen, cyano, C₁-C₃alkoxy,C₁-C₃haloalkoxy, allyloxy, propargyloxy, C₁-C₃alkylthio,C₁-C₃-alkylsulfinyl, C₁-C₃alkylsulfonyl or C₁-C₃alkylsulfonyloxy and R₀₁is as defined under formula I are novel and therefore likewise form partof the subject matter of the present invention.

Preferred compounds of the formula Ila correspond to the formula Ia

in which Q_(a) is hydroxyl, halogen , cyano or a group —CH₂(CO)R₃₆ or

R₀₁ and R₃₆ are as defined in claim 1 and R_(a) is C₁-C₃alkyl.

The compounds of the formula I or compositions comprising them can beused according to the invention in all the application methods customaryin agriculture, for example pre-emergence application, postemergenceapplication and seed dressing, and various methods and techniques, forexample controlled release of active compounds. To this end, the activecompound is absorbed in solution onto mineral granule carriers orpolymerized granules (urea/formaldehyde) and dried. If appropriate, acoating which allows the active compound to be released in metered formover a certain period of time can additionally be applied (coatedgranules).

The compounds of the formula I can be employed as herbicides inunchanged form, i.e. as they are obtained in the synthesis, but they arepreferably processed in a customary manner with the auxiliariesconventionally used in the art of formulation, for example to giveemulsifiable concentrates, directly sprayable or dilutable solutions,dilute emulsions, wettable powders, soluble powders, dusts, granules ormicrocapsules. Such formulations are described, for example, in WO97/34485 on pages 9 to 13. The methods of application, such as spraying,atomizing, dusting, wetting, scattering or watering, in the same way asthe nature of the compositions, are chosen according to the aims strivenfor and the given circumstances.

The formulations, i.e. the compositions, formulations or preparationscomprising the active compound of the formula I or at least one activecompound of the formula I and as a rule one or more solid or liquidformulation auxiliaries, are prepared in a known manner, for example byintimate mixing and/or grinding of the active compounds with theformulation auxiliaries, for example solvents or solid carriers.Surface-active compounds (surfactants) can furthermore additionally beused during the preparation of the formulations. Examples of solventsand solid carriers are given, for example, in WO 97/34485 on page 6.Depending on the nature of the active compound of the formula I to beformulated, suitable surface-active compounds are nonionic, cationicand/or anionic surfactants and surfactant mixtures having goodemulsifying, dispersing and wetting properties.

Examples of suitable anionic, nonionic and cationic surfactants arelisted, for example, in WO 97/34485 on pages 7 and 8.

The surfactants conventionally used in the art of formulation and whichare suitable to prepare the herbicidal compositions according to theinvention are described, inter alia, in “Mc Cutcheon's Detergents andEmulsifiers Annual”, MC Publishing Corp., Ridgewood N.J., 1981, Stache,H., “Tensid-Taschenbuch” [Surfactant handbook], Carl Hanser Verag,Munich/Vienna, 1981 and M. and J. Ash, “Encyclopedia of Surfactants”,Vol I-III, Chemical Publishing Co., New York, 1980-81.

The herbicidal formulations as a rule comprise 0.1 to 99% by weight, inparticular 0.1 to 95% by weight, of herbicide, 1 to 99.9% by weight, inparticular 5 to 99.8% by weight, of a solid or liquid formulationauxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, ofa surfactant. While concentrated compositions are rather preferred ascommercial goods, the end user as a rule uses dilute compositions. Thecompositions can also comprise further additives, such as stabilizers,for example epoxidized or non-epoxidized vegetable oils (epoxidizedcoconut oil, rapeseed oil or soya oil), defoamers, for example siliconeoil, preservatives, viscosity regulators, binders, tackifiers andfertilizers or other active compounds.

The active compounds of the formula I are as a rule applied to theplants or their habitat, at application rates of 0.001 to 4 kg/ha, inparticular 0.005 to 2 kg tha. The dosage required for the desired effectcan be determined by tests. It depends on the nature of the effect, thedevelopment stage of the crop plant and the weed and on the application(location, time, process) and can, as a function of these parameters,vary within wide ranges.

The compounds of the formula I have herbicidal and growth-inhibitingproperties, owing to which they can be used in crops of useful plants,in particular in cereals, cotton, soya, sugar beet, sugar cane,plantings, rapeseed, maize and rice, and for the non-selective controlof weeds. Crops include those which have been rendered tolerant towardsherbicides or herbicide classes by conventional breeding methods orgenetical engineering methods. The weeds to be controlled can be bothmonocotyledonous and dicotyledonous weeds, for example Stellaria,Nasturtium, Agrostis, Digitaria, Avena, Setaria,Sinapis, Lolium,Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus,Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida,Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Violaand Veronica.

The examples below illustrate the invention in more detail, withoutlimiting it.

PREPARATION EXAMPLES Example H1 PreParation of2-difluoromethoxy-6-trifluoromethylnicotinic acid

At 70° C., 25 g (0.106 mol ) of(3-(ethoxycarbonyl)-6-trifluoromethyl)pyrid-2-one (Helv. Chim. Acta(1988), 71(3), 596 601) in a mixture of 50 ml of dimethylformamide and20 ml of water are treated, in the presence of 16 g (0.116 mol) offinely powdered potassium carbonate and with efficient stirring, with acontinuous stream of gaseous Freon-22. After 6 hours, a further 16 g ofpotassium carbonate and 20 ml of dimethyl sulfoxide are added, and themixture is stirred with continuous introduction of Freon-22 gas at atemperature of 100° C for another 4 hours. The mixture is then treatedwith water and ice and extracted with diethyl ether. The aqueous phaseis adjusted to pH 2 using conc. HCl and extracted with ethyl acetate.Diethyl ether is added to the extract, and some(3-(carboxy)-6-trifluoromethyl)pyrid-2-one crystals which haveprecipitated out are removed by filtration. The filtrate is filteredthrough a silica gel column (mobile phase ethyl acetate/hexane 1:1)giving, as a crystalline product, pure2-difluoromethoxy-6-trifluoromethylnicotinic acid: ¹H NMR (CDCl₃, ppm):8.60, d, J=9 Hz, 1H; 7.62, d, J=9 Hz, 1H; 7.62, t, J=67 Hz, 1H.

Example H2 Preparation of 4-methyl-6-trifluoromethylnicotinic Acid

In the presence of 5.8 ml of phenyl dichlorophosphate, 7.5 g (0.03 mol)of ((3-ethoxycarbonyl)-4-methyl-6-trifluoromethyl)pyrid-2-one (Helv.Chim. Acta (1988), 71 (3), 596-601) are heated in a pressure vessel at atemperature of 170° C. for 3 hours. The cold reaction solution isfiltered directly through a short silica gel column (mobile phase: ethylacetate/hexane 1:9), giving, as an oily product, ethyl2-chloro-4-methyl-6-trifluoromethylpyridin-3-ylcarboxylate:

¹H NMR (CDCl₃, ppm): 7.49, s, 1H; 4.48, q, 2H; 2.43, s, 3H, 1.43, t, 3H.

3.0 g (16.8 mmol) of the above product and, in 2 portions, a total of 5g of ammonium formate are added to a suspension of 0.55 g of 10% Pd/C in20 ml of methanol, and the mixture is stirred at room temperature for 24hours. The reaction mixture is then filtered through Celite and, afteraddition of sodium chloride solution, extracted with ethyl acetate.Chromatographic purification (mobile phase 1:9) gives the4-methyl-6-trifluoromethylpyridin-3-yl ethyl ester as an oil: ¹H NMR(CDCl₃, ppm): 9.11, s, 1H; 7.56, s, 1H, 4.44, q, 2H; 2.72, s, 3H, 1.42,t, 3H. This is hydrolysed at 40° C. in the presence of aqueous potassiumhydroxide solution in dioxane. Extraction with ethyl acetate gives,after acidification to pH 2.7, 4-methyl-6-trifluoromethyinicotinic acidas a crystalline product: ¹H NMR (CDCl₃, ppm): 7.49, s, 1H; 4.48, q, 2H;2.43, s, 3H, 1.43, t, 3H; 9.32, s, 1 H, 7.62, s, 1 H, 2.79, s, 3H.

Example H3 Preparation of 6-chloro-4-trifluoromethylnicotinic Acid

9.6 g (0.047 mol) of methyl 4-trifluoromethylpyridin-3-ylcarboxylate,dissolved in 50 ml of dichloromethane, are treated with 30% hydrogenperoxide/urea adduct and 17 ml of trifluoroacetic anhydride. Thereaction solution is stirred at temperature of 20° C. for 20 hours andthen washed once each with dilute sodium hydroxide solution andhalf-saturated sodium chloride solution. The product obtained is3-methoxycarbonyl4-trifluoromethyl-3-pyridine N-oxide; ¹H NMR (CDCl₃,ppm): 8.55, s, 1H; 8.31, d, 1H; 7.6, d, 1H; 3.98, s, 3H. 4.85 g (0.022mol) of the above product are then added to a mixture of 5 ml ofphosphorus oxychloride and 4.3 ml of ethyidiisopropylamine in 15 ml of1,2dichloroethane, and the mixture is heated to a temperature of 60° C.After about 2 hours, another 2 ml of phosphorus oxychloride and 2.8 mlof ethyidiisopropylamine are added, and the mixture is stirred at thistemperature for 20 hours. The reaction mixture is subsequently added toice-water, adjusted to pH 3 using 30% NaOH and then extracted with dichioromethane. Filtration through a little silica gel gives anapproximately 5:1 product mixture of the two 6-chloro- and2-chloro-4-trifluoromethylpyridin-3-yl methyl esters, which can beseparated by HPLC into the pure components. Thus, pure methyl6-chloro-4-trifluoromethylpyridin-3-ylcarboxylate is obtained as themain product; ¹H NMR (CDCl₃, ppm): 8.91, s, 1H; 7.68, s, 1H; 3.98, s,3H, and pure methyl 2-chloro-4-trifluoromethylpyridin-3-ylcarboxylate isobtained as the byproduct; ¹H NMR (CDCl₃, ppm): 8.64, d, 1H; 7.52, d,1H; 4.01, s, 3H. In the presence of 0.073 g of potassium hydroxide, 0.22g of pure methyl 6-chloro-4-trifluoromethylpyridin-3-ylcarboxylate arehydrolysed at room temperature in a 1:1 mixture of 6 ml ofdioxane/water. Recrystallization gives the pure6-chloro-4-trifluoromethyinicotinic acid: m.p. 115-117° C.; ¹H NMR(CDCl₃, ppm): 9.12, s, 1H; 7.24, s, 1H.

Example H4 Preparation of 6-methylthio-4-trifluoromethyinicotinic Acid

In boiling acetone, 0.70 g (2.9 mol) of methyl6-chloro-4-trifluoromethylpyridin-3-ylcarboxylate is treated in thepresence of a catalytic amount of 18-crown-6 with methanethiolate (0.33g) until no further conversion can be detected by gas chromatographicanalysis. The mixture is then filtered through silica gel andevaporated. This gives 0.73 g of methyl6-methylthio-4-trifluoromethylpyridin-3-yicarboxylate; ¹H NMR (CDCl₃,ppm): 8.98, s, 1H; 7.48, S, 1H; 3.94, s, 3H; 2.64, s, 3H. Hydrolysisunder the conditions mentioned above gives6-methylthio-4-trifluoromethylnicotinic acid: ¹H NMR (CDCl₃, ppm): 9.02,s, 1H; 7.46, s, 1H; 2.64, s, 3H.

Example H5 6-Hydroxy-2-trifluoromethylpyridin-3-yl ethyl ester

Under an atmosphere of nitrogen and with stirring, 33.4 g of3,4-dihydro-5-ethoxycarbonyl-6-trifluoromethylpyridin-2-one (Org. Res.&Devel. 1,370 (1997)) and 34 g of manganese dioxide in 250 ml of1,2-dichlorobenzene are heated under reflux for 24 hours. In intervalsof about 20 hours, manganese dioxide (total amount of MnO₂ used: 213 g)is added six more times over a period of 3 days, and the mixture is ineach case heated further under ref lux. The mixture is then cooled,diluted with ethyl acetate, and filtered through silica gel, thefiltercake is washed with ethyl ester and the filtrate is concentrated.The solid residue (26.7 g, i.e. 80%), which may still contain about 6%of starting material, is directly reacted further. For completepurification, it is possible to purify, for example, over silica gel(hexane/ethyl acetate 7:3) (¹H NMR, CDCl₃, ppm): 8.02 (d, 1H); 6.85 (d,1H); 4.86 (q, 2H); 1.37 (t, 1H).

Example H6 Preparation of ethyl 6-chloro-2-trifluoromethylpvridin-3-ylcarboxylate

In a bomb tube, 23.5 g of ethyl6-hydroxy-2trifluoromethylpyridin-3-ylcarboxylate and 23.5 ml of phenyldichlorophosphate are heated at 170° C. for 3 hours, and the mixture is,after cooling, added to ice-water, stirred for a few minutes andsubsequently taken up in ethyl acetate and made slightly alkaline usingsodium bicarbonate and then washed neutral with water. The extracts areadmixed with a little hexane and filtered through silica gel. Thefiltrate is evaporated, leaving 21.6 g (85%) of the title compound inthe form of a dark oil with n_(D) ³⁰, 1.4679. ¹H NMR (CDCl₃, ppm): 8.09(d,1H); 7.60 (d,1 H); 4.43 (q, 2H); 1.43 (t,3H).

Example H7 Preparation of6-chloro-2-trifluoromethylpyridin-3-ylcarboxylic acid

2.5 g of the ethyl 6-chloro-2-trifluoromethylpyridin-3-ylcarboxylateobtained above are dissolved in the smallest possible amount oftetrahydrofuran, treated with approximately 20 g of ice and 11 ml of 1Nlithium hydroxide and stirred at room temperature until hydrolysedcompletely. The mixture is then washed with a little ether and theaqueous phase is acidified using 4N hydrochloric acid and extracted withethyl acetate. The extracts are washed with sodium chloride solution,dried and evaporated. This gives 1.8 g of the title compound of m.p.154-156° C. The other free carboxylic acids are likewise obtained fromtheir esters in this manner.

Example H8 Preparation of ethyl6-methylthio-2-trifiuoromethylpyridin-3-ylcarboxylate

Under an atmosphere of nitrogen and with stirring, a solution of 1.7 gof 6-chloro-2-trifluoromethylpyridin-3-yl ethyl ester in 60 ml ofdimethylformamide is treated a little at a time with 0.52 g of sodiummethanethiolate and stirred at room temperature until the reaction hasgone to completion. The reaction mixture is then poured into ice-water,made neutral by addition of a little dilute hydrochloric acid andextracted with ethyl acetate. The extracts are diluted with a littlehexane, washed with water, dried over sodium sulfate, filtered and,after filtration through a little silica gel, evaporated. This gives 1.4g (79%) of the title compound in the form of an oil with n_(D) ²⁵1.5100, ¹H NMR (CDCl₃, ppm): 7.90 (d, 1H); 7.40 (d, 1H); 1.40 (q, 2H);2.60 (s, 3H); 1.49 (t, 3H).

Example H9 Preparation of ethyl6-ethylthio-2-trifluoromethylpyridin-3-ylcarboxylate

In an apparatus previously flushed with nitrogen, a solution of 1.8 mlof ethanethiol in 40 ml of dimethylformamide, which had been cooled to0° C., is treated a little at a time with 0.96 g of sodium hydride oildispersion (60%), and the mixture is stirred at room temperature. Afterevolution of hydrogen has ceased, the mixture is cooled to −20° C., anda solution of 5.07 g of 6-chloro-2-trifluoromethylpyridin-3-yl ethylester in 10 ml of dimethylformamide is added dropwise at thistemperature, and the mixture is stirred slowly until room temperaturehas been reached. After the reaction has ended (approximately 3 hours),the reaction mixture is added to ice-water and extracted with ethylacetate. The extracts are washed with water, dried, filtered, evaporatedand dried under high vacuum. This gives 5.0 g (89%) of the titlecompound as a brownish oil. ¹H NMR (CDCl₃, ppm): 7.90 (d, 1H); 7.35 (d,1H); 4.40 (q, 2H); 3.25 (q, 2H); 1.38 (2t, 6H).

Example H10 Preparation of ethyl6-ethylsulfinyl-2-trifluoromethylpyridin-3-ylcarboxylate

Under an atmosphere of nitrogen and with stirring and cooling, asolution of 2.5 g of m-chloroperbenzoic acid in 40 ml of methylenechloride is added dropwise at a temperature of −20° C. to a solution of2.8 g of ethyl 6-ethylthio-2-trifluoromethylpyridin-3-ylcarboxylate,which had been charged initially, and the mixture is stirred at atemperature of +5° C. for 20 hours. The mixture is then evaporatedgently and purified over silica gel (hexanelethyl acetate 7:3). Thisgives 2.48 g (84%) of6-ethylsulfinyl-2-trifluoromethylpyridin-3-yl-ethyl ester. ¹H NMR(CDCl₃, ppm): 8.38 (d, 1H); 8.30 (d, 1H); 4.45 (q, 2H); 3.26-3.00 (m,2H); 1.43 (t, 3H); 1.26 (t, 3H).

Ethyl 6-methylsulfinyl-2-trifluoromethylpyridin-3-ylcarboxylate isobtained in an analogous manner.

Example H11 Preparation of ethyl6-methylsulfonyl-2-trifluoromethylpyridin-3-ylcarboxylate

Under an atmosphere of nitrogen and with stirring and cooling, 21 g ofm-chloroperbenzoic acid are introduced a little at a time over a periodof 30 minutes at a temperature of −20° C. into a solution of 3.6 g of6-methylthio-2-trifluoromethylpyridin-3-yl ethyl ester, which had beencharged initially, and the reaction mixture is stirred at roomtemperature for 5 hours. The mixture is then evaporated and filteredthrough silica gel (ethyl acetate/methanol/triethylamine 85:10:5). Thisgives 3.95 g (97%) of ethyl6-methylsulfonyl-2-trifluoromethylpyridin-3-ylcarboxylate as a brownishsolid with m.p. 70-72° C. ¹H NMR (CDCl₃, ppm): 8.40 (1H,d); 8.33 (1H,d);4.47 (2H,q); 1.43 (3H,t).

Example H12 Preparation of ethyl6-cyano-2-trifluoromethylpyridin-3-ylcarboxylate

Under an atmosphere of nitrogen and with stirring, a solution of 0.596 gof ethyl 6-methylsulfonyl-2-trifluoromethylpyridin-3-ylcarboxylate in 5ml of dimethylformamide is treated with 160 mg of solid potassiumcyanide and a spatula tipful of 18-crown-6, and the mixture is heated at80° C. for 3 hours. The mixture is cooled overnight, and the next dayanother 30 mg of potassium cyanide are added and the mixture is heatedfurther until the starting material has disappeared (approximately 2hours). The mixture is then cooled, added to ice-water and extractedwith ethyl acetate. The extracts are washed with water, dried,evaporated and freed from traces of dimethylformamide under high vacuumat approximately 40° C. This gives 480 mg (yield virtually quantitative)of ethyl 6-cyano-2-trifluoromethylpyridin-3-ylcarboxylate in the form ofan oil which slowly solidifies. ¹H NMR (CDCl₃, ppm): 8.29 (1H,d); 7.97(1H,d); 4.48 (2H, d); 1.43 (3H,t).

Example H13 Preparation of ethyl6-methyl-2-trifluoromethylpyridin-3-ylcarboxylate

Under an atmosphere of nitrogen and with stirring, a solution of 3.6 gof 6-chloro-2-trifluoromethylpyridin-3-yl ethyl ester in 20 ml ofdimethylacetamide is treated with 4.5 ml of tetramethyltin and 200 mg ofdichloro(bistriphenylphosphine)palladium, and the mixture is heated to atemperature of 80-90° C. for 24 hours. Then another 1.5 ml oftetramethyltin and 30 mg of dichloro(bistriphenylphosphine)palladium areadded and the mixture is heated for another 6 hours. The reactionmixture is then freed from excess tetramethyltin using reduced pressure(destruction by passing through ethanolic sodium hydroxide solution),cooled and added to ice-water. The mixture is extracted with diethylether and the extract is washed with water, dried over sodium sulfate,filtered through a little silica gel, evaporated and dried under reducedpressure. This gives the title compound (2.4 g, 73%), which stillcontains traces of dimethylacetamide, in the form of a dark oil. ¹H NMR(CDCl₃, ppm): 8.00 (1H,d); 7.42 (1H,d); 4.42 (2H, d); 2.68 (3H, s); 1.41(3H,t). Hydrolysis analogously to the description already mentionedabove affords 6-methyl-2-trifluoromethylpyridin-3-ylcarboxylic acid(brown resin) which is directly converted further into the carbonylchloride.

Example H14 Preparation of 6-methyl-2-trifluoromethylpvridin-3-ylcarbonyl chloride

A solution of 0.45 g of 6-methyl-2-trifluoromethylpyridin-3-ylcarboxyiic acid in 20 ml of dichloromethane is charged initially, 3 drops ofdimethylformamid c are added and the mixture is subsequently treatedwith 1.6 ml of oxalyl chloride. After the intensive evolution of gas hasceased, the mixture is kept at a bath temperature of 40° C. for another1.5 hours and then evaporated. The crude product (0.56 g) that remainsas residue can be directly reacted further. ¹H NMR (CDCl₃, ppm): 8.20(1H,d); 7.51 (1H,d); 2.65 (3H, s).

Example H15 Preparation of 4-oxobicyclo[3.2.1]oct-2-en-2-yl 6-methyl-2-trifluoromethylnicotinate

Under an atmosphere of nitrogen and with stirring and cooling, asolution of 0.56 g of 6-methyl-2-trifluoromethylpyridin-3-ylcarbonylchloride in 10 ml of methylene chloride is added dropwise at 0° C. to asolution of 0.4 g of bicyclo[3.2.1]octane-2,4-dione and 0.72 g oftriethylamine in 10 ml of methylene chloride, and the mixture is stirredfor 5 hours until room temperature has been reached. The mixture is thendiluted with methylene chloride, washed with cold 1N hydrochloric acid,dried and evaporated to give the desired enol ester (0.8 g) as a brownresin which is directly reacted further. ¹H NMR (CDCl₃, ppm): 8.17(1H,d); 7.51 (1H, d); 5.96 (1H, s); 3.04 (2H, m); 2.75 (3H, s);2.32-1.30(m).

Example H16 Preparation of4-hydroxy-3-(6-methyl-2-trifluoromethylpyridin-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-one

Under an atmosphere of nitrogen and with stirring, 0.8 g of the aboveenol ester is dissolved in 30 ml of acetonitrile at 25° C., and themixture is treated with 0.5 ml of triethylamine and 0.4 ml of acetonecyanohydrin and stirred at room temperature for 20 hours. The mixture isthen diluted with solvent and washed with dilute hydrochloric acid,dried and evaporated, and the residue is purified through a littlesilica gel (ethyl acetate/methanol/triethylamine 85:10:5). This gives371 mg (46%) of the title compound (triethylamine salt) in the form of ayellowish resin. ¹H NMR (CDCl₃, ppm): 7.45 (1H, d); 7.25 (1H, d);3.80-3.43 (4H, m); 3.18 (6H, m); 2.80 (2H, s(br)); 2.62 (3H, s);220-1.54 (m).

Example H17 Preparation of ethyl6-methoxy-2-trifluoromethylpyridin-3-ylcarboxylate

A suspension of 5.65 g of ethyl6-hydroxy-2-trifluoromethylpyridin-3-ylcarboxylate, 6.0 g of potassiumcarbonate and 2.7 ml of methyl iodide is, together with a spatula tipfulof 18-crown-6, heated to a temperature of 60-70° C. until the reactionhas gone to completion. The mixture is then filtered, the filtrationresidue is washed with acetonitrile and the filtrate is concentratedunder reduced pressure. The residue is cooled, admixed with ice-water,neutralized with dilute sulfuric acid and extracted with ethyl acetate.The extracts are washed with water, dried, diluted with a little hexaneand filtered through a little silica gel.

The resulting residue is the title compound (3.7 g, 65%) in the form ofslightly orange crystals of m.p. 150-152° C.

¹H NMR (CDCl₃, ppm): 8.00 (1H, d); 6.83 (1H, d); 4.38 (2H, q); 4.01 (3H,s);1.39 (3H, t).

Example H18 Preparation of4-hydroxy-3(2-methyl-6-trifluoromethylpyridin-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-one

6.68 g (0.0305 mol) of methyl 2-methyl-6-trifluoromethyinicotinate(prepared as described in Heterocycles, 46, 129 (1997)) are dissolved in250 ml of methanovwater (3:1 mixture), and 1.92 g (0.046 mol) of lithiumhydroxide hydrate are added a little at a time at 22° C. After 4 hoursat 22° C, the reaction mixture is poured into ethyl acetate and 2Nhydrochloric acid, the organic phase is washed three times with water,dried with sodium sulfate and evaporated and the residue is trituratedwith a little hexane. Filtration gives 5.69 g (90% of theory) of theexpected 2-methyl-6-trifluoromethyinicotinic acid of m.p. 147-149° C.The 2-methyl6trifluoromethyinicotinic acid obtained (2.0 g, 0.0098 mol)is dissolved in 20 ml of oxalyl chloride. Three drops ofdimethylformamide are added, and the mixture is heated under reflux for1 hour. The mixture is then concentrated using a rotary evaporator, andthe residue (2-methyl-6-trifluoromethyinicotinoyl chloride) is taken upin 30 ml of methylene chloride. At 0° C., 2.7 ml (0.0196 mol) oftriethylamine and 0.12 g (0.00098 mol) of dimethylaminopyridine areadded. 1.49 g (0.0108 mol) of bicyclo[3.2.1]octane-2,4-dione, dissolvedin 20 ml of methylene chloride, are then added dropwise. After 3 hoursat 22° C., the reaction mixture is extracted with 2 N hydrochloric acid.The methylene chloride phase is separated off, washed with water andsubsequently extracted with 10% aqueous sodium bicarbonate solution,dried over sodium sulfate and evaporated. This gives 3.18 g (100% oftheory) of 4-oxobicyclo[3.2.1]oct-2-en-2-yl2-methyl-6-trifluoromethyinicotinate as an oil, which can be processedfurther without purification.

3.02 g (0.0093 mol) of 4-oxobicyclo [3.2.1]oct-2en-2-yl2-methyl-6-trifluoromethyinicotinate and 1.9 ml (0.0136 mo l) oftriethylamine are dissolved in 45 ml of acetonitrile. At 22° C., 0.01 mlof acetone cyanohydrin are added. After 18 hours at 22° C., the reactionmixture is poured into dilute hydrochloric acid and extracted with ethylacetate. The ethyl acetate phase is washed with water and then withbrine, dried over sodium sulfate and evaporated, and the residue isdissolved in a little warm acetone. The product crystallizes onstanding. Filtration gives 0.99 g (33% of theory) of the expected4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-oneas white crystals (m.p. 75-77° C.).

Example H19 Preparation of3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-4-oxo-bicyclo[3.2.1]oct-2-en-2-ylbenzoate

At 0° C., a solution of 0.562 g (0.0004 mol) of benzoyl chloride in 1 mlof tetrahydrofuran is added to a solution of 1.14 g (0.0035 mol) of4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-oneand 0.517 g (0.004 mol) of ethyidiisopropylamine in 15 ml oftetrahydrofuran. The reaction mixture is stirred at 25° C. for 2 hours,evaporated and purified over silica gel (hexane/ethyl acetate 1:1). Thisgives 0.9 g (60%) of the title compound in the form of a yellowishresin. ¹H NMR (CDCl₃, ppm): 7.91-7.87, m, 3H; 7.64, t, J=7.5 Hz, 1 H;7.5 0-7.40, m, 3H; 3.24, br t, J=4 Hz, 1 H; 3.14, br t, J=4 Hz, 1H;2.70, s, 3H; 2.47, d, J=13.5 Hz, 1H; 2.40, 2.15, m, 3H; 1.95-1.8, m, 2H.

Example H20 Preparation of4-hydroxy-3-(2-methyl-1-oxy-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one

16.25 g (0.05 mol) of4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-oneand 9.4 g (0.1 mol) of urea/hydrogen peroxide complex are dissolved in150 ml of methylene chloride, and 20.5 ml (0.15 mol) of trifluoroaceticanhydride are added dropwise at 25° C. After 14 hours at 25° C., thereaction mixture is added to ethyl acetate and water, and the organicphase is washed twice with water, dried with sodium sulfate andevaporated. The residue is chromatographed over silica gel (mobilephase: ethyl acetatelmethanol 9/1). This gives 6.8 g (40%) of thedesired product as white crystals (m.p. 109-110° C.).

Example H21 Preparation of4-chloro-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-one

20.15 g (0.062 mo l) of4-hydroxy-3-(2-methyl-6-trifluoromethyipyridine-3carbonyl)-bicyclo[3.2.1]oct-3-en-2-oneare suspended in 50 ml of oxalyl chloride, and 0.1 ml ofdimethylformamide are added dropwise. After the intensive evolution ofgas has ceased, the mixture is kept at a bath temperature of 45° C. foranother 1.5 hours and then evaporated, and the residue is suspended in alittle ethyl acetate and admixed with stirring at 0° C. with hexane.Filtration gives 19.19 g (90% of theory) of4-chloro-3-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-oneof m.p. 137-138° C.

Example H22 Preparation of4-amino-3-(2-methyl-6-trifluoronmethvlpvridine-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2one

1.0 g (0.0029 mol) of4-chloro-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-oneare dissolved in 10 ml of tetrahydrofuran and, at 25° C., treated with2.0 ml of aqueous ammonia (30%). After 0.5 hours at 25° C., the reactionmixture is added to ethyl acetate and water, the organic phase is washedtwice with water, dried with sodium sulfate and evaporated and theresidue is triturated with a little ethyl acetate. Filtration gives 0.81g (86% of theory) of4-amino-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3en-2-onein the form of white crystals (m.p. 262-263° C). ¹H NMR (CDCl₃, ppm):10.62 br s 1H; 8.223 br s 1H; 7.41, d, J=8.1 Hz, 1H; 7.35, d, J=8.1 Hz,1H; 3.03, br t, J=4.8 Hz, 1H; 2.70, br t, J=4.8 Hz, 1H; 2.41, s, 3H;1.97-2.14, m, 3H; 1.77-1.812, m, 1H; 1.47-1.70, m, 2H.

Example H23 Preparation of4-(4-chlorophenylsulfanyl)-3-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one

2.0 g (0.0058 mol) of4-chloro-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-one,0.07 g of dimethylaminopyridine (0.00058 mol) and 1.61 ml oftriethylamine are dissolved in 15 ml of methylene chloride. At 25° C.,0.092 g (0.0064 mol) of 4-chlorothiophenol are added. After 2 hours at22° C., the reaction mixture is evaporated and purified over silica gel(hexane/ethyl acetate 2:1). Recrystallization (hexane/acetic acid at−25° C.) gives pure4-(4-chlorophenylsulfanyl)-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one:m.p. 130-131 ° C.

Example H24 Preparation of4-(4-chlorobenzenesulfonyl)-3-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one

0.6 g (0.00133 mol) of the 4-(4-chlorophenylsultanyl)-3-(2-methyl-6trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-oneobtained above is dissolved in methylene chloride, and 0.9 ml ofperacetic acid (39% in acetic acid, 0.0053 mol) are added dropwise at25° C. After 5 hours at 25° C., the reaction mixture is added to ethylacetate and water, the organic phase is washed with water, dried withsodium sulfate and evaporated and the residue is triturated with alittle hexane. Filtration gives 0.56 g (84% of theory) of4-(4-chlorobenzenesulfonyl)-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-onein the form of white crystals (m.p.166-167° C.).

Example H25 Preparation of(5-cyclopropyl-3-methylsulfanylisoxazol-4-yl)-(2-methyl-6-trifluoromethylpyridin-3-yl)methanoneandcyclopropyl-[3-methylsulfanyl-5-(2-methyl-6-trifluoromethylpyridin-3-yl)isoxazol4-yl)methanone

14.8 g (0.080 mol) of tert-butyl 3-cyclopropyl-3-oxopropionic acid esterare dissolved in 25 ml of MeOH, and 1.93 g (0 .080 mol) of magnesium areadded. With ice-bath cooling, 7 ml of carbon tetrachloride are addeddropwise, and the reaction mixture is stirred at a temperature of 22° C.for one hour. After evaporation, the residue is suspended in 100 ml ofacetonitrile, and 16.31 g (0.073 mol) of2-methyl-6-trifluoromethyinicotinoyl chloride (prepared as described inExample H18), dissolved in 50 ml of acetonitrile, are added dropwise ata temperature of 22° C. After 6 hours, the reaction mixture is taken upin ethyl acetate and washed with saturated sodium bicarbonate solution.The ethyl acetate phase is separated off, washed with water, dried oversodium sulfate and evaporated. The residue is dissolved in 160 ml ofmethylene chloride, and 10 ml of trifluoroacetic acid are added dropwiseat a temperature of 22° C. After 18 hours, the reaction mixture ispoured into water and extracted with methylene chloride. The methylenechloride phase is washed with water and then with saturated aqueoussodium chloride solution, dried over sodium sulfate and evaporated. Thisgives 17.3 g (88% of theory) of1-cyclopropyl-3-(2-methyl-6-trifluoromethylpyridin-3-yl)propane-1,3-dioneas an oil, which is processed further without purification. The1-cyclopropyl-3-(2-methyl-6-trifluoromethylpyridin-3-yl)propane-1,3-dioneobtained above (15.0 g, 0.055 mol) is dissolved in 150 ml ofdimethylformamide, and 50 g of potassium fluoride on an aluminium oxidesupport (alumina) (0.0055 movg, 0.276 mol) are added a little at a timeat a temperature of 0° C. After 5 minutes, 6.7 g (0.088 mol) of carbondisulfide are added dropwise. After 2 hours, 23.6 g (0.166 mol) ofmethyl iodide are added dropwise, and the reaction mixture is warmed toa temperature of 22° C. After a further 2 hours, the alumina is filteredoff, the filtrate is added to water and the mixture is extracted withethyl acetate. The ethyl acetate phase is washed with water and thenwith saturated aqueous sodium chloride solution, dried over sodiumsulfate and evaporated. The residue is chromatographed over silica gel(mobile phase: ethyl acetate/hexane 15/1). This gives 12.0 g (60% oftheory) of2-(bismethylsulfanylmethylene)-1-cyclopropyl-3-(2-methyl-6-trifluoromethylpyridin-3-yl)-propane-1,3-dioneas a solid. 12.0 g (0.033 mol) of the product obtained above are,together with 5.4 g (0.066 mol) of anhydrous sodium acetate, suspendedin 120 ml of ethanol. 4.6 g (0.066 mol) of hydroxylamine hydrochlorideare added, and the reaction mixture is kept at a temperature of 22° C.for 5 hours. Another 2.7 g of anhydrous sodium acetate and 2.3 g ofhydroxylamine hydrochloride are then added. After 18 hours, the reactionmixture is diluted with water and extracted with ethyl acetate. Theethyl acetate phase is washed with water and then with saturated aqueoussodium chloride solution, dried over sodium sulfate and evaporated.Trituration with a little ethyl acetate gives 9.0 g (79.5%) of thedesired product as a 2:1 isomer mixture in the form of white crystals(m.p. 103-104° C.).

Main isomer: ¹H NMR (CDCl₃, ppm)((5-cyclopropyl-3-methylsulfanylisoxazol-4-yl)-(2-methyl-6-trifluoromethylpyridin-3-yl)methanone)7.98, d, J=7.8 Hz, 1H; 7.61, d, J=7.8 Hz, 1H; 2.67, s, 3H; 2.50, s, 3H;2.02-1.93, m, 1 H; 1.34-1.28, m, 2H; 1.18-1.09, m, 2H.

¹H NMR (CDCl₃, ppm)(cyclopropyl-13-methylsulfanyl-5-(2-methyl6-trifluoromethylpyridin-3-yl)isoxazol-4-yl]methane):7.95, d, J=7.8 Hz, 1H; 7.69, d, J=7.8 Hz, 1H; 2.67, s, 3H; 2.66, s, 3H;1.74-1.64, m, 1H; 1.28-1.18, m, 2H; 0.89 4.80, m, 2H.

Example H26 Preparation of(5-cyclopropyl-3-methylsulfinylisoxazol-4-yl)-(2-methyl-6-trifluoromethylpyridin-3-yl)methanoneandcylopropyl-[3-methanesulfinyl-5-(2-methyl-6-trifluoromethylpyridin-3-yl)isoxazol-4-yl]methanone

1.50 g (0.0043 mol) of the isomer mixture obtained above are dissolvedin 30 ml of acetonelwater (2:1 mixture), and 1.02 g (0.0048 mol) ofsodium metaperiodate are added a little at a time at 22° C. After 5hours, the reaction mixture is evaporated using a rotary evaporator. Theresidue is taken up in water and ethyl acetate. The ethyl acetate phaseis dried over sodium sulfate and evaporated. The residue ischromatographed over silica gel (mobile phase: ethyl acetate/hexane3/1). This gives initially 0.8 g (51% of theory) of(5-cyclopropyl-3-methylsulfinylisoxazol-4-yl)-(2-methyl-6-trifluoromethylpyridin-3-yl)methanoneas white crystals (m.p. 96-97° C.). ¹H NMR (CDCl₃, ppm): 7.86, d, J=7.8Hz, 1H; 7.59, d, J=7.8 Hz, 1H; 3.078, s, 3H; 2.66, s, 3H; 1.54-1A49, m,IH; 1.32-1.25, m, 2H; 1.13-1.072, m, 2H.

The second product that eiutes consists of 0.34 g (22% of theory) ofcyclopropyl-[3-methanesulfinyl-5-(2-methyl-6-trifluoromethylpyridin-3yl)isoxazol4-yl]methanoneas white crystals (m.p. 112-113° C.). ¹H NMR (CDCl₃, ppm): 7.97, d,J=7.8 Hz, 1H; 7.67, d, J=7.8 Hz, 1H; 3.128, s, 3H; 2.62, s, 3H;1.69-1.64, m, 1H; 1.26-1.18, m, 2H; 0.90-0.85, m, 2H.

Example H27 Preparation of(5-cyclopropyl-3-methanesulfonylisoxazol-4-yl)-(2-isopropyl-6-trifluoromethylpyridin-3-yl)methanone

0.15 g (0.0045 mol) of(5-cyclopropyl-3-methylsulfanylisoxazol-4-yl)-(2-isopropyl-6-trifluoromethylpyridin-3-yl)methanoneis dissolved in methylene chloride, and 0.28 ml of peracetic acid (39%in acetic acid, 0.0016 mol) are added dropwise at a temperature of 5° C.After 15 hours at 25° C., the reaction mixture is added to ethyl acetateand water, and the organic phase is washed with water, dried with sodiumsulfate and evaporated. The residue is chromatographed over silica gel(mobile phase: ethyl acetate/hexane 5/1). This gives 0.121 g (74% oftheory) of the expected product as white crystals (m.p.105-106° C.).

In an analogous manner, and according to the methods shown in thegeneral reaction schemes 1-10 and in the references mentioned therein,it is also possible to prepare the compounds listed in the tables below.In these tables, CCH is the ethynyl group, Ph is the phenyl group and Meis the methyl group.

TABLE 1

Comp. No. R₁ R₂ R₃ R₄ R₅ p 1.001 H CF₃ H H OH 0 1.002 F CF₃ H H OH 01.003 Cl CF₃ H H OH 0 1.004 Br CF₃ H H OH 0 1.005 CHF₂ CF₃ H H OH 01.006 CCl₃ CF₃ H H OH 0 1.007 CClF₂ CF₃ H H OH 0 1.008 CF₃ CF₃ H H OH 01.009 CH₃ CF₃ H H OH 0 1.01 CH₂CH₃ CF₃ H H OH 0 1.011 CH(CH₃)₂ CF₃ H HOH 0 1.012 (CH₂)₂CH₃ CF₃ H H OH 0 1.013 C(CH₃)₃ CF₃ H H OH 0 1.014 PhCF₃ H H OH 0 1.015 CH₂F CF₃ H H OH 0 1.016 CH₂Cl CF₃ H H OH 0 1.017CH₂Br CF₃ H H OH 0 1.018 CH₂OH CF₃ H H OH 0 1.019 CH₂OCOCH₃ CF₃ H H OH 01.02 CH₂OCOPh CF₃ H H OH 0 1.021 CH₂OCH₃ CF₃ H H OH 0 1.022 CH₂OCH₂CH₃CF₃ H H OH 0 1.023 CH₂CH₂OCH₃ CF₃ H H OH 0 1.024 CH₂SMe CF₃ H H OH 01.025 CH₂SOMe CF₃ H H OH 0 1.026 CH₂SO₂Me CF₃ H H OH 0 1.027 CH₂SO₂PhCF₃ H H OH 0 1.028 SCH₂Ph CF₃ H H OH 0 1.029 SOCH₂Ph CF₃ H H OH 0 1.03SO₂CH₂Ph CF₃ H H OH 0 1.031 SCH₃ CF₃ H H OH 0 1.032 SOCH₃ CF₃ H H OH 01.033 SO₂CH₃ CF₃ H H OH 0 1.034 SPh CF₃ H H OH 0 1.035 SOPh CF₃ H H OH 01.036 SO₂Ph CF₃ H H OH 0 1.037 N(CH₃)₂ CF₃ H H OH 0 1.038 CH═CH₂ CF₃ H HOH 0 1.039 CH₂CH═CH₂ CF₃ H H OH 0 1.04 SO₂N(CH₃)₂ CF₃ H H OH 0 1.041ethynyl CF₃ H H OH 0 1.042 cyclopropyl CF₃ H H OH 0 1.043 OCH₃ CF₃ H HOH 0 1.044 OPh CF₃ H H OH 0 1.045 OCHF₂ CF₃ H H OH 0 1.046 CO₂Me CF₃ H HOH 0 1.047 2-furyl CF₃ H H OH 0 1.048 OCH₂ethynyl CF₃ H H OH 0 1.0492-pyridyl CF₃ H H OH 0 1.05 3-pyridyl CF₃ H H OH 0 1.051 4-pyridyl CF₃ HH OH 0 1.052 H CF₃ H H OH 1 1.053 F CF₃ H H OH 1 1.054 Cl CF₃ H H OH 11.055 Br CF₃ H H OH 1 1.056 CHF₂ CF₃ H H OH 1 1.057 CCl₃ CF₃ H H OH 11.058 CClF₂ CF₃ H H OH 1 1.059 CF₃ CF₃ H H OH 1 1.06 CH₃ CF₃ H H OH 11.061 CH₂CH₃ CF₃ H H OH 1 1.062 CH(CH₃)₂ CF₃ H H OH 1 1.063 (CH₂)₂CH₃CF₃ H H OH 1 1.064 C(CH₃)₃ CF₃ H H OH 1 1.065 Ph CF₃ H H OH 1 1.066 CH₂FCF₃ H H OH 1 1.067 CH₂Cl CF₃ H H OH 1 1.068 CH₂Br CF₃ H H OH 1 1.069CH₂OH CF₃ H H OH 1 1.07 CH₂OCOCH₃ CF₃ H H OH 1 1.071 CH₂OCOPh CF₃ H H OH1 1.072 CH₂OCH₃ CF₃ H H OH 1 1.073 CH₂OCH₂CH₃ CF₃ H H OH 1 1.074CH₂CH₂OCH₃ CF₃ H H OH 1 1.075 CH₂SMe CF₃ H H OH 1 1.076 CH₂SOMe CF₃ H HOH 1 1.077 CH₂SO₂Me CF₃ H H OH 1 1.078 CH₂SO₂Ph CF₃ H H OH 1 1.079SCH₂Ph CF₃ H H OH 1 1.08 SOCH₂Ph CF₃ H H OH 1 1.081 SO₂CH₂Ph CF₃ H H OH1 1.082 SCH₃ CF₃ H H OH 1 1.083 SOCH₃ CF₃ H H OH 1 1.084 SO₂CH₃ CF₃ H HOH 1 1.085 SPh CF₃ H H OH 1 1.086 SOPh CF₃ H H OH 1 1.087 SO₂Ph CF₃ H HOH 1 1.088 N(CH₃)₂ CF₃ H H OH 1 1.089 CH═CH₂ CF₃ H H OH 1 1.09 CH₂CH═CH₂CF₃ H H OH 1 1.091 SO₂N(CH₃)₂ CF₃ H H OH 1 1.092 ethynyl CF₃ H H OH 11.093 cyclopropyl CF₃ H H OH 1 1.094 OCH₃ CF₃ H H OH 1 1.095 OPh CF₃ H HOH 1 1.096 OCHF₂ CF₃ H H OH 1 1.097 CO₂Me CF₃ H H OH 1 1.098 2-furyl CF₃H H OH 1 1.099 OCH₂CCH CF₃ H H OH 1 1.1 2-pyridyl CF₃ H H OH 1 1.1013-pyridyl CF₃ H H OH 1 1.102 4-pyridyl CF₃ H H OH 1 1.103 H CF₂CF₃ H HOH 0 1.104 Cl CF₂CF₃ H H OH 0 1.105 CHF₂ CF₂CF₃ H H OH 0 1.106 CCl₃CF₂CF₃ H H OH 0 1.107 CClF₂ CF₂CF₃ H H OH 0 1.108 CF₃ CF₂CF₃ H H OH 01.109 CH₃ CF₂CF₃ H H OH 0 1.11 CH₂CH₃ CF₂CF₃ H H OH 0 1.111 CH(CH₃)₂CF₂CF₃ H H OH 0 1.112 (CH₂)₂CH₃ CF₂CF₃ H H OH 0 1.113 C(CH₃)₃ CF₂CF₃ H HOH 0 1.114 CH₂F CF₂CF₃ H H OH 0 1.115 CH₂Cl CF₂CF₃ H H OH 0 1.116 CH₂OHCF₂CF₃ H H OH 0 1.117 CH₂OCOCH₃ CF₂CF₃ H H OH 0 1.118 CH₂OCOPh CF₂CF₃ HH OH 0 1.119 CH₂OCH₃ CF₂CF₃ H H OH 0 1.12 CH₂OCH₂CH₃ CF₂CF₃ H H OH 01.121 CH₂SMe CF₂CF₃ H H OH 0 1.122 CH₂SOMe CF₂CF₃ H H OH 0 1.123CH₂SO₂Me CF₂CF₃ H H OH 0 1.124 CH₂SO₂Ph CF₂CF₃ H H OH 0 1.125 N(CH₃)₂CF₂CF₃ H H OH 0 1.126 CH═CH₂ CF₂CF₃ H H OH 0 1.127 CH₂CH═CH₂ CF₂CF₃ H HOH 0 1.128 SO₂N(CH₃)₂ CF₂CF₃ H H OH 0 1.129 CCH CF₂CF₃ H H OH 0 1.13cyclopropyl CF₂CF₃ H H OH 0 1.131 OPh CF₂CF₃ H H OH 0 1.132 OCH₃ CF₂CF₃H H OH 0 1.133 CO₂Me CF₂CF₃ H H OH 0 1.134 OCH₂CCH CF₂CF₃ H H OH 0 1.1352-pyridyl CF₂CF₃ H H OH 0 1.136 3-pyridyl CF₂CF₃ H H OH 0 1.1374-pyridyl CF₂CF₃ H H OH 0 1.138 H CF₂CF₃ H H OH 1 1.139 Cl CF₂CF₃ H H OH1 1.14 CHF₂ CF₂CF₃ H H OH 1 1.141 CCl₃ CF₂CF₃ H H OH 1 1.142 CClF₂CF₂CF₃ H H OH 1 1.143 CF₃ CF₂CF₃ H H OH 1 1.144 CH₃ CF₂CF₃ H H OH 11.145 CH₂CH₃ CF₂CF₃ H H OH 1 1.146 CH(CH₃)₂ CF₂CF₃ H H OH 1 1.147(CH₂)₂CH₃ CF₂CF₃ H H OH 1 1.148 C(CH₃)₃ CF₂CF₃ H H OH 1 1.149 CH₂FCF₂CF₃ H H OH 1 1.15 CH₂Cl CF₂CF₃ H H OH 1 1.151 CH₂OH CF₂CF₃ H H OH 11.152 CH₂OCOCH₃ CF₂CF₃ H H OH 1 1.153 CH₂OCOPh CF₂CF₃ H H OH 1 1.154CH₂OCH₃ CF₂CF₃ H H OH 1 1.155 CH₂OCH₂CH₃ CF₂CF₃ H H OH 1 1.156 CH₂SMeCF₂CF₃ H H OH 1 1.157 CH₂SOMe CF₂CF₃ H H OH 1 1.158 CH₂SO₂Me CF₂CF₃ H HOH 1 1.159 CH₂SO₂Ph CF₂CF₃ H H OH 1 1.16 N(CH₃)₂ CF₂CF₃ H H OH 1 1.161CH═CH₂ CF₂CF₃ H H OH 1 1.162 CH₂CH═CH₂ CF₂CF₃ H H OH 1 1.163 SO₂N(CH₃)₂CF₂CF₃ H H OH 1 1.164 CCH CF₂CF₃ H H OH 1 1.165 cyclopropyl CF₂CF₃ H HOH 1 1.166 OPh CF₂CF₃ H H OH 1 1.167 OCH₃ CF₂CF₃ H H OH 1 1.168 CO₂MeCF₂CF₃ H H OH 1 1.169 OCH₂CCH CF₂CF₃ H H OH 1 1.17 2-pyridyl CF₂CF₃ H HOH 1 1.171 3-pyridyl CF₂CF₃ H H OH 1 1.172 4-pyridyl CF₂CF₃ H H OH 11.173 H CF₂CF₂CF₃ H H OH 0 1.174 CHF₂ CF₂CF₂CF₃ H H OH 0 1.175 CF₃CF₂CF₂CF₃ H H OH 0 1.176 CH₃ CF₂CF₂CF₃ H H OH 0 1.177 CH₂CH₃ CF₂CF₂CF₃ HH OH 0 1.178 (CH₂)₂CH₃ CF₂CF₂CF₃ H H OH 0 1.179 CH₂Cl CF₂CF₂CF₃ H H OH 01.18 CH₂OCH₃ CF₂CF₂CF₃ H H OH 0 1.181 H CF₂CF₂CF₃ H H OH 1 1.182 CHF₂CF₂CF₂CF₃ H H OH 1 1.183 CF₃ CF₂CF₂CF₃ H H OH 1 1.184 CH₃ CF₂CF₂CF₃ H HOH 1 1.185 CH₂CH₃ CF₂CF₂CF₃ H H OH 1 1.186 (CH₂)₂CH₃ CF₂CF₂CF₃ H H OH 01.187 CH₂Cl CF₂CF₂CF₃ H H OH 1 1.188 CH₂OCH₃ CF₂CF₂CF₃ H H OH 1 1.189 HCF₂Cl H H OH 0 1.19 Cl CF₂Cl H H OH 0 1.191 CHF₂ CF₂Cl H H OH 0 1.192CCl₃ CF₂Cl H H OH 0 1.193 CClF₂ CF₂Cl H H OH 0 1.194 CF₃ CF₂Cl H H OH 01.195 CH₃ CF₂Cl H H OH 0 1.196 CH₂CH₃ CF₂Cl H H OH 0 1.197 CH(CH₃)₂CF₂Cl H H OH 0 1.198 (CH₂)₂CH₃ CF₂Cl H H OH 0 1.199 C(CH₃₎ ₃ CF₂Cl H HOH 0 1.2 CH₂F CF₂Cl H H OH 0 1.201 CH₂Cl CF₂Cl H H OH 0 1.202 CH₂OHCF₂Cl H H OH 0 1.203 CH₂OCOCH₃ CF₂Cl H H OH 0 1.204 CH₂OCOPh CF₂Cl H HOH 0 1.205 CH₂OCH₃ CF₂Cl H H OH 0 1.206 CH₂OCH₂CH₃ CF₂Cl H H OH 0 1.207CH₂SMe CF₂Cl H H OH 0 1.208 CH₂SOMe CF₂Cl H H OH 0 1.209 CH₂SO₂Me CF₂ClH H OH 0 1.21 CH₂SO₂Ph CF₂C H H OH 0 1.211 N(CH₃)₂ CF₂Cl H H OH 0 1.212CH═CH₂ CF₂Cl H H OH 0 1.213 CH₂CH═CH₂ CF₂Cl H H OH 0 1.214 SO₂N(CH₃)₂CF₂Cl H H OH 0 1.215 CCH CF₂Cl H H OH 0 1.216 cyclopropyl CF₂Cl H H OH 01.217 OPh CF₂Cl H H OH 0 1.218 OCH₃ CF₂Cl H H OH 0 1.219 CO₂Me CF₂Cl H HOH 0 1.22 OCH₂CCH CF₂Cl H H OH 0 1.221 2-pyridyl CF₂Cl H H OH 0 1.2223-pyridyl CF₂Cl H H OH 0 1.223 4-pyridyl CF₂Cl H H OH 0 1.224 H CF₂Cl HH OH 1 1.225 Cl CF₂Cl H H OH 1 1.226 CHF₂ CF₂Cl H H OH 1 1.227 CCl₃CF₂Cl H H OH 1 1.228 CClF₂ CF₂Cl H H OH 1 1.229 CF₃ CF₂Cl H H OH 1 1.23CH₃ CF₂Cl H H OH 1 1.231 CH₂CH₃ CF₂Cl H H OH 1 1.232 CH(CH₃)₂ CF₂Cl H HOH 1 1.233 (CH₂)₂CH₃ CF₂Cl H H OH 1 1.234 C(CH₃₎ ₃ CF₂Cl H H OH 1 1.235CH₂F CF₂Cl H H OH 1 1.236 CH₂Cl CF₂Cl H H OH 1 1.237 CH₂OH CF₂Cl H H OH1 1.238 CH₂OCOCH₃ CF₂Cl H H OH 1 1.239 CH₂OCOPh CF₂Cl H H OH 1 1.24CH₂OCH₃ CF₂Cl H H OH 1 1.241 CH₂OCH₂CH₃ CF₂Cl H H OH 1 1.242 CH₂SMeCF₂Cl H H OH 1 1.243 CH₂SOMe CF₂Cl H H OH 1 1.244 CH₂SO₂Me CF₂Cl H H OH1 1.245 CH₂SO₂Ph CF₂Cl H H OH 1 1.246 N(CH₃)₂ CF₂Cl H H OH 1 1.247CH═CH₂ CF₂Cl H H OH 1 1.248 CH₂CH═CH₂ CF₂Cl H H OH 1 1.249 SO₂N(CH₃)₂CF₂Cl H H OH 1 1.25 CCH CF₂Cl H H OH 1 1.251 cyclopropyl CF₂Cl H H OH 11.252 OPh CF₂Cl H H OH 1 1.253 OCH₃ CF₂Cl H H OH 1 1.254 CO₂Me CF₂Cl H HOH 1 1.255 OCH₂CCH CF₂Cl H H OH 1 1.256 H CCl₃ H H OH 0 1.257 Cl CCl₃ HH OH 0 1.258 CH₃ CCl₃ H H OH 0 1.259 CH₂CH₃ CCl₃ H H OH 0 1.26 CH(CH₃)₂CCl₃ H H OH 0 1.261 (CH₂)₂CH₃ CCl₃ H H OH 0 1.262 CH₂F CCl₃ H H OH 01.263 CH₂Cl CCl₃ H H OH 0 1.264 CH₂OH CCl₃ H H OH 0 1.265 CH₂OCOCH₃ CCl₃H H OH 0 1.266 CH₂OCOPh CCl₃ H H OH 0 1.267 CH₂OCH₃ CCl₃ H H OH 0 1.268CH₂OCH₂CH₃ CCl₃ H H OH 0 1.269 CH₂SMe CCl₃ H H OH 0 1.27 CH₂SOMe CCl₃ HH OH 0 1.271 CH₂SO₂Me CCl₃ H H OH 0 1.272 CH₂SO₂Ph CCl₃ H H OH 0 1.273cyclopropyl CCl₃ H H OH 0 1.274 OPh CCl₃ H H OH 0 1.275 OCH₃ CCl₃ H H OH0 1.276 CO₂Me CCl₃ H H OH 0 1.277 OCH₂OCH CCl₃ H H OH 0 1.278 H CCl₃ H HOH 1 1.279 Cl CCl₃ H H OH 1 1.28 CH₃ CCl₃ H H OH 1 1.281 CH₂CH₃ CCl₃ H HOH 1 1.282 CH(CH₃)₂ CCl₃ H H OH 1 1.283 (CH₂)₂CH₃ CCl₃ H H OH 1 1.284CH₂F CCl₃ H H OH 1 1.285 CH₂Cl CCl₃ H H OH 1 1.286 CH₂OH CCl₃ H H OH 11.287 CH₂OCOCH₃ CCl₃ H H OH 1 1.288 CH₂OCOPh CCl₃ H H OH 1 1.289 CH₂OCH₃CCl₃ H H OH 1 1.29 CH₂OCH₂CH₃ CCl₃ H H OH 1 1.291 CH₂SMe CCl₃ H H OH 11.292 CH₂SOMe CCl₃ H H OH 1 1.293 CH₂SO₂Me CCl₃ H H OH 1 1.294 CH₂SO₂PhCCl₃ H H OH 1 1.295 cyclopropyl CCl₃ H H OH 1 1.296 OPh CCl₃ H H OH 11.297 OCH₃ CCl₃ H H OH 1 1.298 CO₂Me CCl₃ H H OH 1 1.299 OCH₂CCH CCl₃ HH OH 1 1.3 CF₃ CHF₂ H H OH 0 1.301 CH₃ CHF₂ H H OH 0 1.302 CH₂OCH₃ CHF₂H H OH 0 1.303 CH₂Cl CHF₂ H H OH 0 1.304 CH₂F CHF₂ H H OH 0 1.305 CF₃CHF₂ H H OH 1 1.306 CH₃ CHF₂ H H OH 1 1.307 CH₂OCH₃ CHF₂ H H OH 1 1.308CH₂Cl CHF₂ H H OH 1 1.309 CH₂F CHF₂ H H OH 1 1.31 CH₃ CF₃ H CH₃ OH 01.311 CH₃ CF₃ H CH₃ OH 1 1.312 Cl CF₃ H CH₃ OH 0 1.313 CH₃ CF₃ CH₃ H OH0 1.314 CH₃ CF₃ Ph H OH 0 1.315 CH₃ CF₃ Cl H OH 0 1.316 CH₃ CF₃CO₂CH₂CH₃ H OH 0 1.317 CH₃ CF₃ CO₂CH₂Ph H OH 0 1.318 CH₃ CF₃ CH₃ H OH 11.319 CH₃ CF₃ Ph H OH 1 1.32 CH₃ CF₃ Cl H OH 1 1.321 CH₃ CF₃ CO₂CH₂CH₃ HOH 1 1.322 CH₃ CF₃ CO₂CH₂Ph H OH 1 1.323 OCH₃ CF₃ CH₃ H OH 0 1.324CH₂OCH₃ CF₃ CH₃ H OH 0 1.325 CH₂OCH₃ CF₃ Ph H OH 0 1.326 CH₂OCH₃ CF₃ ClH OH 0 1.327 CH₂OCH₃ CF₃ CO₂CH₂CH₃ H OH 0 1.328 CH₂OCH₃ CF₃ CO₂CH₂Ph HOH 0 1.329 CH₂OCH₃ CF₃ CH₃ H OH 1 1.33 CH₂OCH₃ CF₃ Ph H OH 1 1.331CH₂OCH₃ CF₃ Cl H OH 1 1.332 CH₂OCH₃ CF₃ CO₂CH₂CH₃ H OH 1 1.333 CH₂OCH₃CF₃ CO₂CH₂Ph H OH 1 1.334 COOCH₃ H H H OH 0 1.335 CF₃ SCH₃ H H OH 01.336 CH₃ SCH₃ H H OH 0 1.337 CF₃ SOCH₃ H H OH 0 1.338 CH₃ SOCH₃ H H OH0 1.339 CF₃ SO₂CH₃ H H OH 0 1.34 CH₃ SO₂CH₃ H H OH 0 1.341 CF₃ SCH₂CH₃ HH OH 0 1.342 CH₃ SCH₂CH₃ H H OH 0 1.343 CF₃ SOCH₂CH₃ H H OH 0 1.344 CH₃SOCH₂CH₃ H H OH 0 1.345 CF₃ SO₂CH₂CH₃ H H OH 0 1.346 CH₃ SO₂CH₂CH₃ H HOH 0 1.347 CF₃ OCH₃ H H OH 0 1.348 CH₃ OCH₃ H H OH 0 1.349 CF₃ OCH₂CF₃ HH OH 0 1.35 CH₃ OCH₂CF₃ H H OH 0 1.351 CF₃ OCH₂CCH H H OH 0 1.352 CH₃OCH₂CCH H H OH 0 1.353 CF₃ CN H H OH 0 1.354 CH₃ CN H H OH 0 1.355 CF₃Cl H H OH 0 1.356 CF₃ Cl H H O-NEt₃+ 0 1.357 CH₃ Cl H H OH 0 1.358 H ClH H OH 0 1.359 CF₃ OCH₃ H H OH 0 1.36 CH₃ OCH₃ H H OH 0 1.361 CF₃ CH₃ HH OH 0 1.362 H CF₃ H CH₃ OH 0 1.363 H CF₃ H CF₃ OH 0 1.364 H CF₃ HCH₂CH₃ OH 0 1.365 H CF₃ H CF₃ OH 0 1.366 H CF₃ H SCH₃ OH 0 1.367 H CF₃ HSOCH₃ OH 0 1.368 H CF₃ H SO₂CH₃ OH 0 1.369 H CF₃ H Cl OH 0 1.37 H CF₃ HOCH₃ OH 0 1.371 H CH₃ H CF₃ OH 0 1.372 H Cl H CF₃ OH 0 1.373 H OCH₃ HCF₃ OH 0 1.374 H SCH₃ H CF₃ OH 0 1.375 H SOCH₃ H CF₃ OH 0 1.376 CH₃ CF₃H H O-K+ 0 1.377 CH₃ CF₃ H H S(CH₂)₇CH₃ 0 1.378 CH₃ CF₃ H H S(CH₂)₇CH₃ 01.379 CH₃ CF₃ H H SO(CH₂)₇CH₃ 0 1.38 CH₃ CF₃ H H SO₂(CH₂)₇CH₃ 0 1.381CH₃ CF₃ H H SPh 0 1.382 CH₃ CF₃ H H SOPh 0 1.383 CH₃ CF₃ H H SO₂Ph 01.384 CH₃ CF₃ H H NOCH₃ 0 1.385 CH₃ CF₃ H H NOCH₂Ph 0 1.386 CH₃ CF₃ H HNOCH₂CH═CH₂ 0 1.387 CH₃ CF₃ H H NOC(CH₃)₃ 0 1.388 CH₃ CF₃ H H NOCH₂CH₃ 01.389 CH₃ CF₃ H H NCH₂CH₂SH 0 1.39 CH₃ CF₃ H H NN(CH₃)₂ 0 1.391 CH₃ CF₃H H NN(CH₃)C(S)NH₂ 0 1.392 CH₃ CF₃ H H N-morpholino 0 1.393 CH₃ CF₃ H HNHCOCH₃ 0 1.394 CH₃ CF₃ H H NHCO(CH₂)₇CH₃ 0 1.395 CH₃ CF₃ H H NHCOPh 01.396 CH₃ CF₃ H H NHSO₂CH₃ 0 1.397 CH₃ CF₃ H H NH(CO)S(CH₂)₇CH₃ 0 1.398CH₃ CF₃ H H Cl 0 1.399 CH₃ CF₃ H H NH₂ 0 1.4 CH₃ CF₃ H H OCOC(CH₃)₃ 01.401 CH₃ CF₃ H H OCOCH₃ 0 1.402 CH₃ CF₃ H H OCOPh 0 1.403 CH₃ CF₃ H HOCO-cyclopropyl 0 1.404 CH₃ CF₃ H H OCOCH₂CH₃ 0 1.405 CH₃ CF₃ H HOCOCH═CH₂ 0 1.406 CH₃ CF₃ H H OCOCH═CHCH₃ 0 1.407 CH₃ CF₃ H H O(CO)SCH₃0 1.408 CH₃ CF₃ H H O(CO)S(CH₂)₇CH₃ 0 1.409 CH₃ CF₃ H H O(CO)OCH₂CH₃ 01.41 CH₃ CF₃ H H O(CO)N(CH₂CH₃)₂ 0 1.411 CH₃ (CF₂)₃CF₃ H H OH 0 1.412CH₃ CF₃ H H S-(4-Cl-phenyl) 0 1.413 CH₃ CF₃ H H SO-(4-Cl-phenyl) 0 1.414CH₃ CF₃ H H SO₂-(4-Cl-phenyl) 0 1.415 CH₃ CF₃ H H S-(4-CF₃-phenyl) 01.416 CH₃ CF₃ H H SO-(4-CF₃-phenyl) 0 1.417 CH₃ CF₃ H HSO₂-(4-CF₃-phenyl) 0 1.418 CH₃ CF₃ H H S-(4-NO₂-phenyl) 0 1.419 CH₃ CF₃H H SO-(4-NO₂-phenyl) 0 1.42 CH₃ CF₃ H H SO₂-(4-NO₂-phenyl) 0 1.421 CH₃CF₃ H H

0 1.422 CH₃ CF₃ H H

0 1.423 CH₃ CF₃ H H

0 1.424 CH₃ CF₃ H H

0 1.425 CF₂H SCH₃ H H OH 0 1.426 CF₂Cl SCH₃ H H OH 0 1.427 CF₂H SOCH₃ HH OH 0 1.428 CF₂Cl SOCH₃ H H OH 0 1.429 CF₂H SO₂CH₃ H H OH 0 1.43 CF₂ClSO₂CH₃ H H OH 0 1.431 CF₂H SCH₂CH₃ H H OH 0 1.432 CF₂Cl SCH₂CH₃ H H OH 01.433 CF₂H SOCH₂CH₃ H H OH 0 1.434 CF₂Cl SOCH₂CH₃ H H OH 0 1.435 CF₂HSO₂CH₂CH₃ H H OH 0 1.436 CF₂Cl SO₂CH₂CH₃ H H OH 0 1.437 CF₂H OCH₃ H H OH0 1.438 CF₂Cl OCH₃ H H OH 0 1.439 CF₂H OCH₂CF₃ H H OH 0 1.44 CF₂ClOCH₂CF₃ H H OH 0 1.441 CF₂H OCH₂CCH H H OH 0 1.442 CF₂Cl OCH₂CCH H H OH0 1.443 CF₂H CN H H OH 0 1.444 CF₂Cl CN H H OH 0 1.445 CF₂H Cl H H OH 01.446 CF₂Cl Cl H H OH 0 1.447 CF₂H OCH₃ H H OH 0 1.448 CF₂Cl OCH₃ H H OH0 1.449 CF₃ CH₂OCH₃ H H OH 0 1.45 CF₃ CH₂OCH₃ H H OH 1 1.451 CF₂ClCH₂OCH₃ H H OH 0 1.452 CF₂Cl CH₂OCH₃ H H OH 1 1.453 CF₂H CH₂OCH₃ H H OH0 1.454 CF₂H CH₂OCH₃ H H OH 1 1.455 CN CF₃ H H OH 0

TABLE 2

Comp. No. R₁ R₂ R₃ R₄ 2.001 H CF₃ H H 2.002 F CF₃ H H 2.003 Cl CF₃ H H2.004 Br CF₃ H H 2.005 CHF₂ CF₃ H H 2.006 CCl₃ CF₃ H H 2.007 CClF₂ CF₃ HH 2.008 CF₃ CF₃ H H 2.009 CH₃ CF₃ H H 2.01 CH₂CH₃ CF₃ H H 2.011 CH(CH₃)₂CF₃ H H 2.012 (CH₂)₂CH₃ CF₃ H H 2.013 Ph CF₃ H H 2.014 CH₂F CF₃ H H2.015 CH₂Cl CF₃ H H 2.016 CH₂Br CF₃ H H 2.017 CH₂OH CF₃ H H 2.018CH₂OCOCH₃ CF₃ H H 2.019 CH₂OCOPh CF₃ H H 2.02 CH₂OCH₃ CF₃ H H 2.021CH₂OCH₂CH₃ CF₃ H H 2.022 CH₂CH₂OCH₃ CF₃ H H 2.023 CH₂SMe CF₃ H H 2.024CH₂SOMe CF₃ H H 2.025 CH₂SO₂Me CF₃ H H 2.026 CH₂SO₂Ph CF₃ H H 2.027SCH₂ph CF₃ H H 2.028 SOCH₂Ph CF₃ H H 2.029 SO₂CH₂Ph CF₃ H H 2.03 SCH₃CF₃ H H 2.031 SOCH₃ CF₃ H H 2.032 SO₂CH₃ CF₃ H H 2.033 N(CH₃)₂ CF₃ H H2.034 CH═CH₂ CF₃ H H 2.035 CH₂CH═CH₂ CF₃ H H 2.036 SO₂N(CH₃)₂ CF₃ H H2.037 CCH CF₃ H H 2.038 OCH₃ CF₃ H H 2.039 OPh CF₃ H H 2.04 OCHF₂ CF₃ HH 2.041 CO₂Me CF₃ H H 2.042 OCH₂CCH CF₃ H H 2.043 OCH₂CF₃ CF₃ H H 2.044H CF₃ H Cl 2.045

F H Cl 2.046 CN CF₃ H H 2.047 H CHF₂ H H 2.048 CH₃ CHF₂ H H 2.049 CH₂CH₃CHF₂ H H 2.05 CH₂OCH₃ CHF₂ H H 2.051 H CF₂Cl H H 2.052 CH₃ CF₂Cl H H2.053 CH₂CH₃ CF₂Cl H H 2.054 CH₂OCH₃ CF₂Cl H H

TABLE 3

Comp. No. R₁ R₂ R₃ R₄ 3.001 H CF₃ H H 3.002 F CF₃ H H 3.003 Cl CF₃ H H3.004 Br CF₃ H H 3.005 CHF₂ CF₃ H H 3.006 CCl₃ CF₃ H H 3.007 CClF₂ CF₃ HH 3.008 CF₃ CF₃ H H 3.009 CH₃ CF₃ H H 3.01 CH₂CH₃ CF₃ H H 3.011 CH(CH₃)₂CF₃ H H 3.012 (CH₂)₂CH₃ CF₃ H H 3.013 Ph CF₃ H H 3.014 CH₂F CF₃ H H3.015 CH₂Cl CF₃ H H 3.016 CH₂Br CF₃ H H 3.017 CH₂OH CF₃ H H 3.018CH₂OCOCH₃ CF₃ H H 3.019 CH₂OCOPh CF₃ H H 3.02 CH₂OCH₃ CF₃ H H 3.021CH₂OCH₂CH₃ CF₃ H H 3.022 CH₂CH₂OCH₃ CF₃ H H 3.023 CH₂SMe CF₃ H H 3.024CH₂SOMe CF₃ H H 3.025 CH₂SO₂Me CF₃ H H 3.026 CH₂SO₂Ph CF₃ H H 3.027SCH₂Ph CF₃ H H 3.028 SOCH₂Ph CF₃ H H 3.029 SO₂CH₂Ph CF₃ H H 3.03 SCH₃CF₃ H H 3.031 SOCH₃ CF₃ H H 3.032 SO₂CH₃ CF₃ H H 3.033 N(CH₃)₂ CF₃ H H3.034 CH═CH₂ CF₃ H H 3.035 CH₂CH═CH₂ CF₃ H H 3.036 SO₂N(CH₃)₂ CF₃ H H3.037 CCH CF₃ H H 3.038 OCH₃ CF₃ H H 3.039 OPh CF₃ K H 3.04 OCHF₂ CF₃ HH 3.041 CO₂Me CF₃ H H 3.042 OCH₂CCH CF₃ H H 3.043 OCH₂CF₃ CF₃ H H 3.044H CF₃ H H 3.045 CN CF₃ H H 3.046 H CHF₂ H H 3.047 CH₃ CHF₂ H H 3.048CH₂CH₃ CHF₂ H H 3.049 CH₂OCH₃ CHF₂ H H 3.05 H CF₂Cl H H 3.051 CH₃ CF₂ClH H 3.052 CH₂CH₃ CF₂Cl H H 3.053 CH₂OCH₃ CF₂Cl H H 3.054 Cl CH₃ H H3.055 CN SCH₃ H H 3.056 CN SO₂CH₃ H H

TABLE 4

Comp. No. R₁ R₂ R₃ R₄ R₅ P 4.001 H CF₃ H H OH 0 4.002 F CF₃ H H OH 04.003 Cl CF₃ H H OH 0 4.004 Br CF₃ H H OH 0 4.005 CHF₂ CF₃ H H OH 04.006 CCl₃ CF₃ H H OH 0 4.007 CClF₂ CF₃ H H OH 0 4.008 CF₃ CF₃ H H OH 04.009 CH₃ CF₃ H H OH 0 4.01 CH₂CH₃ CF₃ H H OH 0 4.011 CH(CH₃)₂ CF₃ H HOH 0 4.012 (CH₂)₂CH₃ CF₃ H H OH 0 4.013 C(CH₃)₃ CF₃ H H OH 0 4.014 PhCF₃ H H OH 0 4.015 CH₂F CF₃ H H OH 0 4.016 CH₂Cl CF₃ H H OH 0 4.017CH₂Br CF₃ H H OH 0 4.018 CH₂OH CF₃ H H OH 0 4.019 CH₂OCOCH₃ CF₃ H H OH 04.02 CH₂OCOPh CF₃ H H OH 0 4.021 CH₂OCH₃ CF₃ H H OH 0 4.022 CH₂OCH₂CH₃CF₃ H H OH 0 4.023 CH₂CH₂OCH₃ CF₃ H H OH 0 4.024 CH₂SMe CF₃ H H OH 04.025 CH₂SOMe CF₃ H H OH 0 4.026 CH₂SO₂Me CF₃ H H OH 0 4.027 CH₂SO₂PhCF₃ H H OH 0 4.028 N(CH₃)₂ CF₃ H H OH 0 4.029 CH═CH₂ CF₃ H H OH 0 4.03CH₂CH═CH₂ CF₃ H H OH 0 4.031 SO₂N(CH₃)₂ CF₃ H H OH 0 4.032 CCH CF₃ H HOH 0 4.033 cyclopropyl CF₃ H H OH 0 4.034 OCH₃ CF₃ H H OH 0 4.035 OPhCF₃ H H OH 0 4.036 OCHF₂ CF₃ H H OH 0 4.037 CO₂Me CF₃ H H OH 0 4.038OCH₂CCH CF₃ H H OH 0 4.039 H CF₃ H H OH 1 4.04 F CF₃ H H OH 1 4.041 ClCF₃ H H OH 1 4.042 Br CF₃ H H OH 1 4.043 CHF₂ CF₃ H H OH 1 4.044 Cl₃ CF₃H H OH 1 4.045 CClF₂ CF₃ H H OH 1 4.046 CF₃ CF₃ H H OH 1 4.047 CH₃ CF₃ HH OH 1 4.048 CH₂CH₃ CF₃ H H OH 1 4.049 CH(CH₃)₂ CF₃ H H OH 1 4.05(CH₂)₂CH₃ CF₃ H H OH 1 4.051 C(CH₃)₃ CF₃ H H OH 1 4.052 Ph CF₃ H H OH 14.053 CH₂F CF₃ H H OH 1 4.054 CH₂Cl CF₃ H H OH 1 4.055 CH₂Br CF₃ H H OH1 4.056 CH₂OH CF₃ H H OH 1 4.057 CH₂OCOCH₃ CF₃ H H OH 1 4.058 CH₂OCOPhCF₃ H H OH 1 4.059 CH₂OCH₃ CF₃ H H OH 1 4.06 CH₂OCH₂CH₃ CF₃ H H OH 14.061 CH₂CH₂OCH₃ CF₃ H H OH 1 4.062 CH₂SMe CF₃ H H OH 1 4.063 CH₂SOMeCF₃ H H OH 1 4.064 CH₂SO₂Me CF₃ H H OH 1 4.065 CH₂SO₂Ph CF₃ H H OH 14.066 N(CH₃₎ ₂ CF₃ H H OH 1 4.067 CH═CH₂ CF₃ H H OH 1 4.068 CH₂CH═CH₂CF₃ H H OH 1 4.069 SO₂N(CH₃)₂ CF₃ H H OH 1 4.07 CCH CF₃ H H OH 1 4.071cyclopropyl CF₃ H H OH 1 4.072 OCH₃ CF₃ H H OH 1 4.073 OPh CF₃ H H OH 14.074 OCHF₂ CF₃ H H OH 1 4.075 CO₂Me CF₃ H H OH 1 4.076 2-furyl CF₃ H HOH 1 4.077 OCH₂CCH CF₃ H H OH 1 4.078 H CF₂CF₃ H H OH 0 4.079 Cl CF₂CF₃H H OH 0 4.08 CHF₂ CF₂CF₃ H H OH 0 4.081 CCl₃ CF₂CF₃ H H OH 0 4.082CClF₂ CF₂CF₃ H H OH 0 4.083 CF₃ CF₂CF₃ H H OH 0 4.084 CH₃ CF₂CF₃ H H OH0 4.085 CH₂CH₃ CF₂CF₃ H H OH 0 4.086 CH(CH₃)₂ CF₂CF₃ H H OH 0 4.087(CH₂)₂CH₃ CF₂CF₃ H H OH 0 4.088 C(CH₃)₃ CF₂CF₃ H H OH 0 4.089 CH₂FCF₂CF₃ H H OH 0 4.09 CH₂Cl CF₂CF₃ H H OH 0 4.091 CH₂OH CF₂CF₃ H H OH 04.092 CH₂OCOCH₃ CF₂CF₃ H H OH 0 4.093 CH₂OCOPh CF₂CF₃ H H OH 0 4.094CH₂OCH₃ CF₂CF₃ H H OH 0 4.095 CH₂OCH₂CH₃ CF₂CF₃ H H OH 0 4.096 CH₂SMeCF₂CF₃ H H OH 0 4.097 CH₂SOMe CF₂CF₃ H H OH 0 4.098 CH₂SO₂Me CF₂CF₃ H HOH 0 4.099 CH₂SO₂Ph CF₂CF₃ H H OH 0 4.1 N(CH₃)₂ CF₂CF₃ H H OH 0 4.101CH═CH₂ CF₂CF₃ H H OH 0 4.102 CH₂CH═CH₂ CF₂CF₃ H H OH 0 4.103 SO₂N(CH₃)₂CF₂CF₃ H H OH 0 4.104 CCH CF₂CF₃ H H OH 0 4.105 cyclopropyl CF₂CF₃ H HOH 0 4.106 OPh CF₂CF₃ H H OH 0 4.107 OCH₃ CF₂CF₃ H H OH 0 4.108 CO₂MeCF₂CF₃ H H OH 0 4.109 OCH₂CCH CF₂CF₃ H H OH 0 4.11 H CF₂CF₂CF₃ H H OH 04.111 CHF₂ CF₂CF₂CF₃ H H OH 0 4.112 CF₃ CF₂CF₂CF₃ H H OH 0 4.113 CH₃CF₂CF₂CF₃ H H OH 0 4.114 CH₂CH₃ CF₂CF₂CF₃ H H OH 0 4.115 (CH₂)₂CH₃CF₂CF₂CF₃ H H OH 0 4.116 CH₂Cl CF₂CF₂CF₃ H H OH 0 4.117 CH₂OCH₃CF₂CF₂CF₃ H H OH 0 4.118 H CF₂Cl H H OH 0 4.119 Cl CF₂Cl H H OH 0 4.12CHF₂ CF₂Cl H H OH 0 4.121 CCl₃ CF₂Cl H H OH 0 4.122 CClF₂ CF₂Cl H H OH 04.123 CF₃ CF₂Cl H H OH 0 4.124 CH₃ CF₂Cl H H OH 0 4.125 CH₂CH₃ CF₂Cl H HOH 0 4.126 CH(CH₃)₂ CF₂Cl H H OH 0 4.127 (CH₂)₂CH₃ CF₂Cl H H OH 0 4.128C(CH₃)₃ CF₂Cl H H OH 0 4.129 CH₂F CF₂Cl H H OH 0 4.13 CH₂Cl CF₂Cl H H OH0 4.131 CH₂OH CF₂Cl H H OH 0 4.132 CH₂OCOCH₃ CF₂Cl H H OH 0 4.133CH₂OCOPh CF₂Cl H H OH 0 4.134 CH₂OCH₃ CF₂Cl H H OH 0 4.135 CH₂OCH₂CH₃CF₂Cl H H OH 0 4.136 CH₂SMe CF₂Cl H H OH 0 4.137 CH₂SOMe CF₂Cl H H OH 04.138 CH₂SO₂Me CF₂Cl H H OH 0 4.139 CH₂SO₂Ph CF₂Cl H H OH 0 4.14 N(CH₃)₂CF₂Cl H H OH 0 4.141 CH═CH₂ CF₂Cl H H OH 0 4.142 CH₂CH═CH₂ CF₂Cl H H OH0 4.143 SO₂N(CH₃)₂ CF₂Cl H H OH 0 4.144 CCH CF₂Cl H H OH 0 4.145cyclopropyl CF₂Cl H H OH 0 4.146 OPh CF₂Cl H H OH 0 4.147 OCH₃ CF₂Cl H HOH 0 4.148 CO₂Me CF₂Cl H H OH 0 4.149 OCH₂CCH CF₂Cl H H OH 0 4.15 CH₃CF₂Cl H H OH 1 4.151 CH₂OCH₃ CF₂Cl H H OH 1 4.152 H CCl₃ H H OH 0 4.153Cl CCl₃ H H OH 0 4.154 CH₃ CCl₃ H H OH 0 4.155 CH₂CH₃ CCl₃ H H OH 04.156 CH(CH₃)₂ CCl₃ H H OH 0 4.157 (CH₂)₂CH₃ CCl₃ H H OH 0 4.158 CH₂FCCl₃ H H OH 0 4.159 CH₂Cl CCl₃ H H OH 0 4.16 CH₂OH CCl₃ H H OH 0 4.161CH₂OCOCH₃ CCl₃ H H OH 0 4.162 CH₂OCOPh CCl₃ H H OH 0 4.163 CH₂OCH₃ CCl₃H H OH 0 4.164 CH₂OCH₂CH₃ CCl₃ H H OH 0 4.165 CH₂SMe CCl₃ H H OH 0 4.166CH₂SOMe CCl₃ H H OH 0 4.167 CH₂SO₂Me CCl₃ H H OH 0 4.168 CH₂SO₂Ph CCl₃ HH OH 0 4.169 cyclopropyl CCl₃ H H OH 0 4.17 OPh CCl₃ H H OH 0 4.171 OCH₃CCl₃ H H OH 0 4.172 CO₂Me CCl₃ H H OH 0 4.173 OCH₂CCH CCl₃ H H OH 04.174 CF₃ CHF₂ H H OH 0 4.175 CH₃ CHF₂ H H OH 0 4.176 CH₂OCH₃ CHF₂ H HOH 0 4.177 CH₂Cl CHF₂ H H OH 0 4.178 CH₂F CHF₂ H H OH 0 4.179 CF₃ CHF₂ HH OH 1 4.18 CH₃ CHF₂ H H OH 1 4.181 CH₂OCH₃ CHF₂ H H OH 1 4.182 CH₂ClCHF₂ H H OH 1 4.183 CH₂F CHF₂ H H OH 1 4.184 CH₃ CF₃ H CH₃ OH 0 4.185CH₃ CF₃ H CH₃ OH 1 4.186 Cl CF₃ H CH₃ OH 0 4.187 CH₃ CF₃ CH₃ H OH 04.188 CH₃ CF₃ Ph H OH 0 4.189 CH₃ CF₃ Cl H OH 0 4.19 CH₃ CF₃ CO₂CH₂CH₃ HOH 0 4.191 CH₃ CF₃ CO₂CH₂Ph H OH 0 4.192 CH₃ CF₃ CH₃ H OH 1 4.193 CH₃CF₃ Ph H OH 1 4.194 CH₃ CF₃ Cl H OH 1 4.195 CH₃ CF₃ CO₂CH₂CH₃ H OH 14.196 CH₃ CF₃ OC₂CH₂Ph H OH 1 4.197 OCH₃ CF₃ CH₃ H OH 0 4.198 CH₂OCH₃CF₃ CH₃ H OH 0 4.199 CH₂OCH₃ CF₃ Ph H OH 0 4.2 CH₂OCH₃ CF₃ Cl H OH 04.201 CH₂OCH₃ CF₃ CO₂CH₂CH₃ H OH 0 4.202 CH₂OCH₃ CF₃ CO₂CH₂Ph H OH 04.203 CH₂OCH₃ CF₃ CH₃ H OH 1 4.204 CH₂OCH₃ CF₃ Ph H OH 1 4.205 CH₂OCH₃CF₃ Cl H OH 1 4.206 CH₂OCH₃ CF₃ CO₂CH₂CH₃ H OH 1 4.207 CH₂OCH₃ CF₃CO₂CH₂Ph H OH 1 4.208 COOCH₃ H H H OH 0 4.209 CF₃ SCH₃ H H OH 0 4.21 CH₃SCH₃ H H OH 0 4.211 CF₃ SOCH₃ H H OH 0 4.212 CH₃ SOCH₃ H H OH 0 4.213CF₃ SO₂CH₃ H H OH 0 4.214 CH₃ SO₂CH₃ H H OH 0 4.215 CF₃ SCH₂CH₃ H H OH 04.216 CH₃ SCH₂CH₃ H H OH 0 4.217 CF₃ SOCH₂CH₃ H H OH 0 4.218 CH₃SOCH₂CH₃ H H OH 0 4.219 CF₃ SO₂CH₂CH₃ H H OH 0 4.22 CH₃ SO₂CH₂CH₃ H H OH0 4.221 CF₃ OCH₃ H H OH 0 4.222 CH₃ OCH₃ H H OH 0 4.223 CF₃ OCH₂CF₃ H HOH 0 4.224 CH₃ OCH₂CF₃ H H OH 0 4.225 CF₃ OCH₂CCH H H OH 0 4.226 CH₃OCH₂CCH H H OH 0 4.227 CF₃ CN H H OH 0 4.228 CH₃ CN H H OH 0 4.229 CF₃Cl H H OH 0 4.23 CH₃ Cl H H OH 0 4.231 H Cl H H OH 0 4.232 CF₃ OCH₃ H HOH 0 4.233 CH₃ OCH₃ H H OH 0 4.234 CF₃ CH₃ H H OH 0 4.235 H CF₃ H CH₃ OH0 4.236 H CF₃ H CF₃ OH 0 4.237 H CF₃ H CH₂CH₃ OH 0 4.238 H CF₃ H CF₃ OH0 4.239 H CF₃ H SCH₃ OH 0 4.24 H CF₃ H SOCH₃ OH 0 4.241 H CF₃ H SO₂CH₃OH 0 4.242 H CF₃ H Cl OH 0 4.243 H CF₃ H OCH₃ OH 0 4.244 H CH₃ H CF₃ OH0 4.245 H Cl H CF₃ OH 0 4.246 H OCH₃ H CF₃ OH 0 4.247 H SCH₃ H CF₃ OH 04.248 H SOCH₃ H CF₃ OH 0 4.249 CH₃ CF₃ H H S(CH₂)₇CH₃ 0 4.25 CH₃ CF₃ H HS(CH₂)₇CH₃ 0 4.251 CH₃ CF₃ H H SO(CH₂)₇CH₃ 0 4.252 CH₃ CF₃ H HSO₂(CH₂)₇CH₃ 0 4.253 CH₃ CF₃ H H SPh 0 4.254 CH₃ CF₃ H H SOPh 0 4.255CH₃ CF₃ H H SO₂Ph 0 4.256 CH₃ CF₃ H H NOCH₃ 0 4.257 CH₃ CF₃ H H NOCH₂Ph0 4.258 CH₃ CF₃ H H NOCH₂CH═CH₂ 0 4.259 CH₃ CF₃ H H NOC(CH₃)₃ 0 4.26 CH₃CF₃ H H NOCH₂CH₃ 0 4.261 CH₃ CF₃ H H NCH₂CH₂SH 0 4.262 CH₃ CF₃ H HNN(CH₃)₂ 0 4.263 CH₃ CF₃ H H NN(CH₃)C(S)NH₂ 0 4.264 CH₃ CF₃ H HN-morpholino 0 4.265 CH₃ CF₃ H H NHCOCH₃ 0 4.266 CH₃ CF₃ H HNHCO(CH₂)₇CH₃ 0 4.267 CH₃ CF₃ H H NHCOPh 0 4.268 CH₃ CF₃ H H NHSO₂CH₃ 04.269 CH₃ CF₃ H H NH(CO)S(CH₂)₇CH₃ 0 4.27 CH₃ CF₃ H H Cl 0 4.271 CH₃ CF₃H H NH₂ 0 4.272 CH₃ CF₃ H H OCOC(CH₃₎ ₃ 0 4.273 CH₃ CF₃ H H OCOCH₃ 04.274 CH₃ CF₃ H H OCOPh 0 4.275 CH₃ CF₃ H H OCO-cyclopropyl 0 4.276 CH₃CF₃ H H OCOCH₂CH₃ 0 4.277 CH₃ CF₃ H H OCOCH═CH₂ 0 4.278 CH₃ CF₃ H HOCOCH═CHCH₃ 0 4.279 CH₃ CF₃ H H O(CO)SCH₃ 0 4.28 CH₃ CF₃ H HO(CO)S(CH₂)₇CH₃ 0 4.281 CH₃ CF₃ H H O(CO)OCH₂CH₃ 0 4.282 CH₃ CF₃ H HO(CO)N(CH₂CH₃)₂ 0 4.283 CH₃ (CF₂)₃CF₃ H H OH 0 4.284 CH₃ CF₃ H HS-(4-Cl-phenyl) 0 4.285 CH₃ CF₃ H H SO-(4-Cl-phenyl) 0 4.286 CH₃ CF₃ H HSO₂-(4-Cl-phenyl) 0 4.287 CH₃ CF₃ H H S-(4-CF₃-phenyl) 0 4288 CH₃ CF₃ HH SO-(4-CF₃-phenyl) 0 4.289 CH₃ CF₃ H H SO₂-(4-CF₃-phenyl) 0 4.29 CH₃CF₃ H H S-(4-NO₂-phenyl) 0 4.291 CH₃ CF₃ H H SO-(4-NO₂-phenyl) 0 4.292CH₃ CF₃ H H SO₂-(4-NO₂-phenyl) 0 4.293 CH₃ CF₃ H H

0 4.294 CH₃ CF₃ H H

0 4.295 CH₃ CF₃ H H

0 4.296 CH₃ CF₃ H H

0 4.297 CF₂H SCH₃ H H OH 0 4.298 CF₂Cl SCH₃ H H OH 0 4.299 CF₂H SOCH₃ HH OH 0 4.3 CF₂Cl SOCH₃ H H OH 0 4.301 CF₂H SO₂CH₃ H H OH 0 4.302 CF₂ClSO₂CH₃ H H OH 0 4.303 CF₂H SCH₂CH₃ H H OH 0 4.304 CF₂Cl SCH₂CH₃ H H OH 04.305 CF₂H SOCH₂CH₃ H H OH 0 4.306 CF₂Cl SOCH₂CH₃ H H OH 0 4.307 CF₂HSO₂CH₂CH₃ H H OH 0 4.308 CF₂Cl SO₂CH₂CH₃ H H OH 0 4.309 CF₂H OCH₃ H H OH0 4.31 CF₂Cl OCH₃ H H OH 0 4.311 CF₂H OCH₂CF₃ H H OH 0 4.312 CF₂ClOCH₂CF₃ H H OH 0 4.313 CF₂H OCH₂CCH H H OH 0 4.314 CF₂Cl OCH₂CCH H H OH0 4.315 CF₂H CN H H OH 0 4.316 CF₂Cl CN H H OH 0 4.317 CF₂H Cl H H OH 04.318 CF₂Cl Cl H H OH 0 4.319 CF₂H OCH₃ H H OH 0 4.32 CF₂Cl OCH₃ H H OH0 4.321 CF₃ CH₂OCH₃ H H OH 0 4.322 CF₃ CH₂OCH₃ H H OH 1 4.323 CF₂ClCH₂OCH₃ H H OH 0 4.324 CF₂Cl CH₂OCH₃ H H OH 1 4.325 CF₂H CH₂OCH₃ H H OH0 4.326 CF₂H CH₂OCH₃ H H OH 1 4.327 CN CF₃ H H OH 0 4.328 SCH₃ H H H OH0

TABLE 5

Comp. No. R₁ R₂ R₃ R₄ R₅ 5.001 H CF₃ H H CH₃ 5.002 F CF₃ H H CH₃ 5.003Cl CF₃ H H CH₃ 5.004 CHF₂ CF₃ H H CH₃ 5.005 CCl₃ CF₃ H H CH₃ 5.006 CClF₂CF₃ H H CH₃ 5.007 CF₃ CF₃ H H CH₃ 5.008 CH₃ CF₃ H H CH₃ 5.009 CH₂CH₃ CF₃H H CH₃ 5.01 CH(CH₃)2 CF₃ H H CH₃ 5.011 (CH₂)₂CH₃ CF₃ H H CH₃ 5.012 CH₂FCF₃ H H CH₃ 5.013 CH₂Cl CF₃ H H CH₃ 5.014 CH₂Br CF₃ H H CH₃ 5.015CH₂OCOCH₃ CF₃ H H CH₃ 5.016 CH₂OCH₃ CF₃ H H CH₃ 5.017 CH₂CH₂OCH₃ CF₃ H HCH₃ 5.018 CH₂SMe CF₃ H H CH₃ 5.019 CH₂SOMe CF₃ H H CH₃ 5.02 CH₂SO₂Me CF₃H H CH₃ 5.021 N(CH₃)₂ CF₃ H H CH₃ 5.022 CH═CH₂ CF₃ H H CH₃ 5.023CH₂CH═CH₂ CF₃ H H CH₃ 5.024 SO₂N(CH₃)₂ CF₃ H H CH₃ 5.025 CCH CF₃ H H CH₃5.026 cyclopropyl CF₃ H H CH₃ 5.027 OCH₃ CF₃ H H CH₃ 5.028 OPh CF₃ H HCH₃ 5.029 OCHF₂ CF₃ H H CH₃ 5.03 CO₂Me CF₃ H H CH₃ 5.031 OCH₂CCH CF₃ H HCH₃ 5.032 CF₃ SCH₃ H H CH₃ 5.033 CH₃ SCH₃ H H CH₃ 5.034 CF₃ SOCH₃ H HCH₃ 5.035 CH₃ SOCH₃ H H CH₃ 5.036 CF₃ SO₂CH₃ H H CH₃ 5.037 CH₃ SO₂CH₃ HH CH₃ 5.038 CF₃ OCH₃ H H CH₃ 5.039 CH₃ OCH₃ H H CH₃ 5.04 CF₃ OCH₂CF₃ H HCH₃ 5.041 CH₃ OCH₂CF₃ H H CH₃ 5.042 CF₃ OCH₂CCH H H CH₃ 5.043 CH₃OCH₂CCH H H CH₃ 5.044 CF₃ CN H H CH₃ 5.045 CH₃ CN H H CH₃ 5.046 CF₃ Cl HH CH₃ 5.047 CH₃ Cl H H CH₃ 5.048 H Cl H H CH₃ 5.049 CF₃ OCH₃ H H CH₃5.05 CH₃ OCH₃ H H CH₃ 5.051 CF₃ CH₃ H H CH₃ 5.052 H CF₃ H CH₃ CH₃ 5.053H CF₃ H CF₃ CH₃ 5.054 H CF₃ H CH₂CH₃ CH₃ 5.055 H CF₃ H CF₃ CH₃ 5.056 HCF₃ H SCH₃ CH₃ 5.057 H CF₃ H SOCH₃ CH₃ 5.058 H CF₃ H SO₂CH₃ CH₃ 5.059 HCF₃ H Cl CH₃ 5.06 H CF₃ H OCH₃ CH₃ 5.061 H CH₃ H CF₃ CH₃ 5.062 H Cl HCF₃ CH₃ 5.063 H OCH₃ H CF₃ CH₃ 5.064 H SCH₃ H CF₃ CH₃ 5.065 H SOCH₃ HCF₃ CH₃ 5.066 CF₂Cl CH₃ H H CH₃ 5.067 CF₂Cl CH₂CH₃ H H CH₃ 5.068 CF₂ClSCH₃ H H CH₃ 5.069 CF₂Cl SOCH₃ H H CH₃ 5.07 CF₂Cl SO₂CH₃ H H CH₃ 5.071CF₂Cl OCH₃ H H CH₃ 5.072 CF₂Cl OCH₂CF₃ H H CH₃ 5.073 CF₂Cl OCH₂CCH H HCH₃ 5.074 CF₂Cl CN H H CH₃ 5.075 CF₂Cl Cl H H CH₃ 5.076 CF₂Cl OCH₃ H HCH₃ 5.077 CF₃ CH₂OCH₃ H H CH₃ 5.078 CF₂Cl CH₂OCH₃ H H CH₃ 5.079 CF₂HCH₂OCH₃ H H CH₃ 5.08 CN CF₃ H H CH₃ 5.081 CH₃ CF₃ H H CH₂CH₃ 5.082 CH₃CF₃ H H SCH₃ 5.083 CH₃ CF₃ H H SOCH₃ 5.084 CH₃ CF₃ H H SO₂CH₃ 5.085 CH₃CF₃ H H H

TABLE 6

Comp. No. R₁ R₂ R₃ R₄ R₅ 6.001 Cl CF₃ H H CH₂CH₃ 6.002 CHF₂ CF₃ H HCH₂CH₃ 6.003 CCl₃ CF₃ H H CH₂CH₃ 6.004 CClF₂ CF₃ H H CH₂CH₃ 6.005 CF₃CF₃ H H CH₂CH₃ 6.006 CH₃ CF₃ H H CH₂CH₃ 6.007 CH₂CH₃ CF₃ H H CH₂CH₃6.008 (CH₂)₂CH₃ CF₃ H H CH₂CH₃ 6.009 CH₂F CF₃ H H CH₂CH₃ 6.01 CH₂Cl CF₃H H CH₂CH₃ 6.011 CH₂OCH₃ CF₃ H H CH₂CH₃ 6.012 CH₂SMe CF₃ H H CH₂CH₃6.013 CH₂SO₂Me CF₃ H H CH₂CH₃ 6.014 CH═CH₂ CF₃ H H CH₂CH₃ 6.015CH₂CH═CH₂ CF₃ H H CH₂CH₃ 6.016 CCH CF₃ H H CH₂CH₃ 6.017 CF₃ SCH₃ H HCH₂CH₃ 6.018 CF₃ SOCH₃ H H CH₂CH₃ 6.019 CF₃ SO₂CH₃ H H CH₂CH₃ 6.02 CF₃OCH₃ H H CH₂CH₃ 6.021 CF₃ CN H H CH₂CH₃ 6.022 CF₃ Cl H H CH₂CH₃ 6.023CF₃ OCH₃ H H CH₂CH₃ 6.024 CF₃ CH₃ H H CH₂CH₃ 6.025 H CF₃ H CH₃ CH₂CH₃6.026 H CF₃ H CF₃ CH₂CH₃ 6.027 H CF₃ H SCH₃ CH₂CH₃ 6.028 H CF₃ H SOCH₃CH₂CH₃ 6.029 H CF₃ H SO₂CH₃ CH₂CH₃ 6.03 H CF₃ H Cl CH₂CH₃ 6.031 H CF₃ HOCH₃ CH₂CH₃ 6.032 H CH₃ H CF₃ CH₂CH₃ 6.033 H Cl H CF₃ CH₂CH₃ 6.034 HOCH₃ H CF₃ CH₂CH₃ 6.035 CN CF₃ H H CH₂CH₃ 6.036 Cl CF₃ H H CH(CH₃)₂6.037 CHF₂ CF₃ H H CH(CH₃)₂ 6.038 CCl₃ CF₃ H H CH(CH₃)₂ 6.039 CClF₂ CF₃H H CH(CH₃)₂ 6.04 CF₃ CF₃ H H CH(CH₃)₂ 6.041 CH₃ CF₃ H H CH(CH₃)₂ 6.042CH₂CH₃ CF₃ H H CH(CH₃)₂ 6.043 (CH₂)₂CH₃ CF₃ H H CH(CH₃)₂ 6.044 CH₂F CF₃H H CH(CH₃)₂ 6.045 CH₂Cl CF₃ H H CH(CH₃)₂ 6.046 CH₂OCH₃ CF₃ H H CH(CH₃)₂6.047 CH₂SMe CF₃ H H CH(CH₃)₂ 6.048 CH₂SO₂Me CF₃ H H CH(CH₃)₂ 6.049CH═CH₂ CF₃ H H CH(CH₃)₂ 6.05 CH₂CH═CH₂ CF₃ H H CH(CH₃)₂ 6.051 CCH CF₃ HH CH(CH₃)₂ 6.052 CF₃ SCH₃ H H CH(CH₃)₂ 6.053 CF₃ SOCH₃ H H CH(CH₃)₂6.054 CF₃ SO₂CH₃ H H CH(CH₃)₂ 6.055 CF₃ OCH₃ H H CH(CH₃)₂ 6.056 CF₃ CN HH CH(CH₃)₂ 6.057 CF₃ Cl H H CH(CH₃)₂ 6.058 CF₃ OCH₃ H H CH(CH₃)₂ 6.059CF₃ CH₃ H H CH(CH₃)₂ 6.06 H CF₃ H CH₃ CH(CH₃)₂ 6.061 H CF₃ H CF₃CH(CH₃)₂ 6.062 H CF₃ H SCH₃ CH(CH₃)₂ 6.063 H CF₃ H SOCH₃ CH(CH₃)₂ 6.064H CF₃ H SO₂CH₃ CH(CH₃)₂ 6.065 H CF₃ H Cl CH(CH₃)₂ 6.066 H CF₃ H OCH₃CH(CH₃)₂ 6.067 H CH₃ H CF₃ CH(CH₃)₂ 6.068 H Cl H CF₃ CH(CH₃)₂ 6.069 HOCH₃ H CF₃ CH(CH₃)₂ 6.07 CN CF₃ H H CH(CH₃)₂ 6.071 Cl CF₃ H H HNPh 6.072CHF₂ CF₃ H H HNPh 6.073 CCl₃ CF₃ H H HNPh 6.074 CClF₂ CF₃ H H HNPh 6.075CF₃ CF₃ H H HNPh 6.076 CH₃ CF₃ H H HNPh 6.077 CH₂CH₃ CF₃ H H HNPh 6.078(CH₂)₂CH₃ CF₃ H H HNPh 6.079 CH₂F CF₃ H H HNPh 6.08 CH₂Cl CF₃ H H HNPh6.081 CH₂OCH₃ CF₃ H H HNPh 6.082 CH₂SMe CF₃ H H HNPh 6.083 CH₂SO₂Me CF₃H H HNPh 6.084 CH═CH₂ CF₃ H H HNPh 6.085 CH₂CH═CH₂ CF₃ H H HNPh 6.086CCH CF₃ H H HNPh 6.087 CF₃ SCH₃ H H HNPh 6.088 CF₃ SOCH₃ H H HNPh 6.089CF₃ SO₂CH₃ H H HNPh 6.09 CF₃ OCH₃ H H HNPh 6.091 CF₃ CN H H HNPh 6.092CF₃ Cl H H HNPh 6.093 CF₃ OCH₃ H H HNPh 6.094 CF₃ CH₃ H H HNPh 6.095 HCF₃ H CH₃ HNPh 6.096 H CF₃ H CF₃ HNPh 6.097 H CF₃ H SCH₃ HNPh 6.098 HCF₃ H SOCH₃ HNPh 6.099 H CF₃ H SO₂CH₃ HNPh 6.1 H CF₃ H Cl HNPh 6.101 HCF₃ H OCH₃ HNPh 6.102 H CH₃ H CF₃ HNPh 6.103 H Cl H CF₃ HNPh 6.104 HOCH₃ H CF₃ HNPh 6.105 CN CF₃ H H HNPh 6.106 Cl CF₃ H H HNC(CH₃)₃ 6.107CHF₂ CF₃ H H HNC(CH₃)₃ 6.108 CCl₃ CF₃ H H HNC(CH₃)₃ 6.109 CClF₂ CF₃ H HHNC(CH₃)₃ 6.11 CF₃ CF₃ H H HNC(CH₃)₃ 6.111 CH₃ CF₃ H H HNC(CH₃)₃ 6.112CH₂CH₃ CF₃ H H HNC(CH₃)₃ 6.113 (CH₂)₂CH₃ CF₃ H H HNC(CH₃)₃ 6.114 CH₂FCF₃ H H HNC(CH₃)₃ 6.115 CH₂Cl CF₃ H H HNC(CH₃)₃ 6.116 CH₂OCH₃ CF₃ H HHNC(CH₃)₃ 6.117 CH₂SMe CF₃ H H HNC(CH₃)₃ 6.118 CH₂SO₂Me CF₃ H HHNC(CH₃)₃ 6.119 CH═CH₂ CF₃ H H HNC(CH₃)₃ 6.12 CH₂CH═CH₂ CF₃ H HHNC(CH₃)₃ 6.121 CCH CF₃ H H HNC(CH₃)₃ 6.122 CF₃ SCH₃ H H HNC(CH₃)₃ 6.123CF₃ SOCH₃ H H HNC(CH₃)₃ 6.124 CF₃ SO₂CH₃ H H HNC(CH₃)₃ 6.125 CF₃ OCH₃ HH HNC(CH₃)₃ 6.126 CF₃ CN H H HNC(CH₃)₃ 6.127 CF₃ Cl H H HNC(CH₃)₃ 6.128CF₃ OCH₃ H H HNC(CH₃)₃ 6.129 CF₃ CH₃ H H HNC(CH₃)₃ 6.13 H CF₃ H CH₃HNC(CH₃)₃ 6.131 H CF₃ H CF₃ HNC(CH₃)₃ 6.132 H CF₃ H SCH₃ HNC(CH₃)₃ 6.133H CF₃ H SOCH₃ HNC(CH₃)₃ 6.134 H CF₃ H SO₂CH₃ HNC(CH₃)₃ 6.135 H CF₃ H ClHNC(CH₃)₃ 6.136 H CF₃ H OCH₃ HNC(CH₃)₃ 6.137 H CH₃ H CF₃ HNC(CH₃)₃ 6.138H Cl H CF₃ HNC(CH₃)₃ 6.139 H OCH₃ H CF₃ HNC(CH₃)₃ 6.14 CN CF₃ H HHNC(CH₃)₃

TABLE 7

Comp. No. R₁ R₂ R₃ R₄ p 7.001 H CF₃ H H 0 7.002 F CF₃ H H 0 7.003 Cl CF₃H H 0 7.004 Br CF₃ H H 0 7.005 CHF₂ CF₃ H H 0 7.006 CCl₃ CF₃ H H 0 7.007CClF₂ CF₃ H H 0 7.008 CF₃ CF₃ H H 0 7.009 CH₃ CF₃ H H 0 7.01 CH₂CH₃ CF₃H H 0 7.011 CH(CH₃)₂ CF₃ H H 0 7.012 (CH₂)₂CH₃ CF₃ H H 0 7.013 C(CH₃)₃CF₃ H H 0 7.014 Ph CF₃ H H 0 7.015 CH₂F CF₃ H H 0 7.016 CH₂Cl CF₃ H H 07.017 CH₂Br CF₃ H H 0 7.018 CH₂OH CF₃ H H 0 7.019 CH₂OCOCH₃ CF₃ H H 07.02 CH₂OCOPh CF₃ H H 0 7.021 CH₂OCH₃ CF₃ H H 0 7.022 CH₂OCH₂CH₃ CF₃ H H0 7.023 CH₂CH₂OCH₃ CF₃ H H 0 7.024 CH₂SMe CF₃ H H 0 7.025 CH₂SOMe CF₃ HH 0 7.026 CH₂SO₂Me CF₃ H H 0 7.027 CH₂SO₂Ph CF₃ H H 0 7.028 SCH₃ CF₃ H H0 7.029 SOCH₃ CF₃ H H 0 7.03 SO₂CH₃ CF₃ H H 0 7.031 N(CH₃)₂ CF₃ H H 07.032 CH═CH₂ CF₃ H H 0 7.033 CH₂CH═CH₂ CF₃ H H 0 7.034 SO₂N(CH₃)₂ CF₃ HH 0 7.035 CCH CF₃ H H 0 7.036 cyclopropyl CF₃ H H 0 7.037 OCH₃ CF₃ H H 07.038 OCHF₂ CF₃ H H 0 7.039 OCH₂CCH CF₃ H H 0 7.04 H CF₂CF₃ H H 0 7.041Cl CF₂CF₃ H H 0 7.042 CHF₂ CF₂CF₃ H H 0 7.043 CCl₃ CF₂CF₃ H H 0 7.044CClF₂ CF₂CF₃ H H 0 7.045 CF₃ CF₂CF₃ H H 0 7.046 CH₃ CF₂CF₃ H H 0 7.047CH₂CH₃ CF₂CF₃ H H 0 7.048 CH(CH₃)₂ CF₂CF₃ H H 0 7.049 (CH₂)₂CH₃ CF₂CF₃ HH 0 7.05 C(CH₃)₃ CF₂CF₃ H H 0 7.051 CH₂F CF₂CF₃ H H 0 7.052 CH₂Cl CF₂CF₃H H 0 7.053 CH₂OH CF₂CF₃ H H 0 7.054 CH₂OCOCH₃ CF₂CF₃ H H 0 7.055CH₂OCOPh CF₂CF₃ H H 0 7.056 CH₂OCH₃ CF₂CF₃ H H 0 7.057 CH₂OCH₂CH₃ CF₂CF₃H H 0 7.058 CH₂SMe CF₂CF₃ H H 0 7.059 CH₂SOMe CF₂CF₃ H H 0 7.06 CH₂SO₂MeCF₂CF₃ H H 0 7.061 CH₂SO₂Ph CF₂CF₃ H H 0 7.062 N(CH₃)₂ CF₂CF₃ H H 07.063 CH═CH₂ CF₂CF₃ H H 0 7.064 CH₂CH═CH₂ CF₂CF₃ H H 0 7.065 SO₂N(CH₃)₂CF₂CF₃ H H 0 7.066 CCH CF₂CF₃ H H 0 7.067 cyclopropyl CF₂CF₃ H H 0 7.068OCH₃ CF₂CF₃ H H 0 7.069 CO₂Me CF₂CF₃ H H 0 7.07 OCH₂CCH CF₂CF₃ H H 07.071 H CF₂Cl H H 0 7.072 Cl CF₂Cl H H 0 7.073 CHF₂ CF₂Cl H H 0 7.074CCl₃ CF₂Cl H H 0 7.075 CClF₂ CF₂Cl H H 0 7.076 CF₃ CF₂Cl H H 0 7.077 CH₃CF₂Cl H H 0 7.078 CH₂CH₃ CF₂Cl H H 0 7.079 CH(CH₃)₂ CF₂Cl H H 0 7.08(CH₂)₂CH₃ CF₂Cl H H 0 7.081 C(CH₃)₃ CF₂Cl H H 0 7.082 CH₂F CF₂Cl H H 07.083 CH₂Cl CF₂Cl H H 0 7.084 CH₂OH CF₂Cl H H 0 7.085 CH₂OCOCH₃ CF₂Cl HH 0 7.086 CH₂OCOPh CF₂Cl H H 0 7.087 CH₂OCH₃ CF₂Cl H H 0 7.088CH₂OCH₂CH₃ CF₂Cl H H 0 7.089 CH₂SMe CF₂Cl H H 0 7.09 CH₂SOMe CF₂Cl H H 07.091 CH₂SO₂Me CF₂Cl H H 0 7.092 CH₂SO₂Ph CF₂Cl H H 0 7.093 N(CH₃)₂CF₂Cl H H 0 7.094 CH═CH₂ CF₂Cl H H 0 7.095 CH₂CH═CH₂ CF₂Cl H H 0 7.096SO₂N(CH₃)₂ CF₂Cl H H 0 7.097 CCH CF₂Cl H H 0 7.098 cyclopropyl CF₂Cl H H0 7.099 OCH₃ CF₂Cl H H 0 7.1 OCH₂CCH CF₂Cl H H 0 7.101 CF₃ CHF₂ H H 07.102 CH₃ CHF₂ H H 0 7.103 CH₂OCH₃ CHF₂ H H 0 7.104 CH₂Cl CHF₂ H H 07.105 CH₂F CHF₂ H H 0 7.106 CH₃ CF₃ H CH₃ 0 7.107 Cl CF₃ H CH₃ 0 7.108CH₃ CF₃ CH₃ H 0 7.109 CH₃ CF₃ Cl H 0 7.11 OCH₃ CF₃ CH₃ H 0 7.111 CH₂OCH₃CF₃ CH₃ H 0 7.112 CH₂OCH₃ CF₃ Cl H 0 7.113 COOCH₃ H H H 0 7.114 CF₃ SCH₃H H 0 7.115 CH₃ SCH₃ H H 0 7.116 CF₃ SOCH₃ H H 0 7.117 CH₃ SOCH₃ H H 07.118 CF₃ SO₂CH₃ H H 0 7.119 CH₃ SO₂CH₃ H H 0 7.12 CF₃ OCH₃ H H 0 7.121CH₃ OCH₃ H H 0 7.122 CF₃ OCH₂CF₃ H H 0 7.123 CH₃ OCH₂CF₃ H H 0 7.124 CF₃OCH₂CCH H H 0 7.125 CH₃ OCH₂CCH H H 0 7.126 CF₃ CN H H 0 7.127 CH₃ CN HH 0 7.128 CF₃ Cl H H 0 7.129 CF₃ Cl H H 0 7.13 CH₃ Cl H H 0 7.131 H Cl HH 0 7.132 CF₃ OCH₃ H H 0 7.133 CH₃ OCH₃ H H 0 7.134 CF₃ CH₃ H H 0 7.135H CF₃ H CH₃ 0 7.136 H CF₃ H CF₃ 0 7.137 H CF₃ H CH₂CH₃ 0 7.138 H CF₃ HCF₃ 0 7.139 H CF₃ H SCH₃ 0 7.14 H CF₃ H SOCH₃ 0 7.141 H CF₃ H SO₂CH₃ 07.142 H CF₃ H Cl 0 7.143 H CF₃ H OCH₃ 0 7.144 H CH₃ H CF₃ 0 7.145 H Cl HCF₃ 0 7.146 H OCH₃ H CF₃ 0 7.147 H SCH₃ H CF₃ 0 7.148 H SOCH₃ H CF₃ 07.149 CH₃ (CF₂)₃CF₃ H H 0 7.15 CF₂H SCH₃ H H 0 7.151 CF₂Cl SCH₃ H H 07.152 CF₂H SOCH₃ H H 0 7.153 CF₂Cl SOCH₃ H H 0 7.154 CF₂H SO₂CH₃ H H 07.155 CF₂Cl SO₂CH₃ H H 0 7.156 CF₂H OCH₃ H H 0 7.157 CF₂Cl OCH₃ H H 07.158 CF₂H OCH₂CF₃ H H 0 7.159 CF₂Cl OCH₂CF₃ H H 0 7.16 CF₂H OCH₂CCH H H0 7.161 CF₂Cl OCH₂CCH H H 0 7.162 CF₂H CN H H 0 7.163 CF₂Cl CN H H 07.164 CF₂H Cl H H 0 7.165 CF₂Cl Cl H H 0 7.166 CF₂H OCH₃ H H 0 7.167CF₂Cl OCH₃ H H 0 7.168 CF₃ CH₂OCH₃ H H 0 7.169 CF₂Cl CH₂OCH₃ H H 0 7.17CF₂H CH₂OCH₃ H H 0 7.171 CN CF₃ H H 0 7.172 H CF₃ H H 2 7.173 F CF₃ H H2 7.174 Cl CF₃ H H 2 7.175 Br CF₃ H H 2 7.176 CHF₂ CF₃ H H 2 7.177 CCl₃CF₃ H H 2 7.178 CClF₂ CF₃ H H 2 7.179 CF₃ CF₃ H H 2 7.18 CH₃ CF₃ H H 27.181 CH₂CH₃ CF₃ H H 2 7.182 CH(CH₃)₂ CF₃ H H 2 7.183 (CH₂)₂CH₃ CF₃ H H2 7.184 C(CH₃)₃ CF₃ H H 2 7.185 Ph CF₃ H H 2 7.186 CH₂F CF₃ H H 2 7.187CH₂Cl CF₃ H H 2 7.188 CH₂Br CF₃ H H 2 7.189 CH₂OH CF₃ H H 2 7.19CH₂OCOCH₃ CF₃ H H 2 7.191 CH₂OCOPh CF₃ H H 2 7.192 CH₂OCH₃ CF₃ H H 27.193 CH₂OCH₂CH₃ CF₃ H H 2 7.194 CH₂CH₂OCH₃ CF₃ H H 2 7.195 CH₂SMe CF₃ HH 2 7.196 CH₂SOMe CF₃ H H 2 7.197 CH₂SO₂Me CF₃ H H 2 7.198 CH₂SO₂Ph CF₃H H 2 7.199 SCH₃ CF₃ H H 2 7.2 SOCH₃ CF₃ H H 2 7.201 SO₂CH₃ CF₃ H H 27.202 N(CH₃)₂ CF₃ H H 2 7.203 CH═CH₂ CF₃ H H 2 7.204 CH₂CH═CH₂ CF₃ H H 27.205 SO₂N(CH₃)₂ CF₃ H H 2 7.206 CCH CF₃ H H 2 7.207 cyclopropyl CF₃ H H2 7.208 OCH₃ CF₃ H H 2 7.209 OCHF₂ CF₃ H H 2 7.21 OCH₂CCH CF₃ H H 2

TABLE 8

Comp. No. R₁ R₂ R₃ R₄ 8.001 H CF₃ H H 8.002 F CF₃ H H 8.003 Cl CF₃ H H8.004 Br CF₃ H H 8.005 CHF₂ CF₃ H H 8.006 CCl₃ CF₃ H H 8.007 CClF₂ CF₃ HH 8.008 CF₃ CF₃ H H 8.009 CH₃ CF₃ H H 8.01 CH₂CH₃ CF₃ H H 8.011 CH(CH₃)₂CF₃ H H 8.012 (CH₂)₂CH₃ CF₃ H H 8.013 C(CH₃)₃ CF₃ H H 8.014 Ph CF₃ H H8.015 CH₂F CF₃ H H 8.016 CH₂Cl CF₃ H H 8.017 CH₂Br CF₃ H H 8.018 CH₂OHCF₃ H H 8.019 CH₂OCOCH₃ CF₃ H H 8.02 CH₂OCOPh CF₃ H H 8.021 CH₂OCH₃ CF₃H H 8.022 CH₂OCH₂CH₃ CF₃ H H 8.023 CH₂CH₂OCH₃ CF₃ H H 8.024 CH₂SMe CF₃ HH 8.025 CH₂SOMe CF₃ H H 8.026 CH₂SO₂Me CF₃ H H 8.027 CH₂SO₂Ph CF₃ H H8.028 SCH₃ CF₃ H H 8.029 SOCH₃ CF₃ H H 8.03 SO₂CH₃ CF₃ H H 8.031 N(CH₃)₂CF₃ H H 8.032 CH═CH₂ CF₃ H H 8.033 CH₂CH═CH₂ CF₃ H H 8.034 SO₂N(CH₃)₂CF₃ H H 8.035 CCH CF₃ H H 8.036 cyclopropyl CF₃ H H 8.037 OCH₃ CF₃ H H8.038 OCHF₂ CF₃ H H 8.039 OCH₂CCH CF₃ H H

TABLE 9

Comp. No. R₁ R₂ R₃ R₄ 9.001 H CF₃ H H 9.002 F CF₃ H H 9.003 Cl CF₃ H H9.004 Br CF₃ H H 9.005 CHF₂ CF₃ H H 9.006 CCl₃ CF₃ H H 9.007 CClF₂ CF₃ HH 9.008 CF₃ CF₃ H H 9.009 CH₃ CF₃ H H 9.01 CH₂CH₃ CF₃ H H 9.011 CH(CH₃)₂CF₃ H H 9.012 (CH₂)₂CH₃ CF₃ H H 9.013 C(CH₃)₃ CF₃ H H 9.014 Ph CF₃ H H9.015 CH₂F CF₃ H H 9.016 CH₂Cl CF₃ H H 9.017 CH₂Br CF₃ H H 9.018 CH₂OHCF₃ H H 9.019 CH₂OCOCH₃ CF₃ H H 9.02 CH₂OCOPh CF₃ H H 9.021 CH₂OCH₃ CF₃H H 9.022 CH₂OCH₂CH₃ CF₃ H H 9.023 CH₂CH₂OCH₃ CF₃ H H 9.024 CH₂SMe CF₃ HH 9.025 CH₂SOMe CF₃ H H 9.026 CH₂SO₂Me CF₃ H H 9.027 CH₂SO₂Ph CF₃ H H9.028 SCH₃ CF₃ H H 9.029 SOCH₃ CF₃ H H 9.03 SO₂CH₃ CF₃ H H 9.031 N(CH₃)₂CF₃ H H 9.032 CH═CH₂ CF₃ H H 9.033 CH₂CH═CH₂ CF₃ H H 9.034 SO₂N(CH₃)₂CF₃ H H 9.035 CCH CF₃ H H 9.036 cyclopropyl CF₃ H H 9.037 OCH₃ CF₃ H H9.038 OCHF₂ CF₃ H H 9.039 OCH₂CCH CF₃ H H

Physical data (melting points in ° C.): Comp. No. 1.001 resin 1.005crystals m.p. 61-62 1.008 oil 1.009 crystals m.p. 75-77 1.01  oil 1.011crystals m.p. 111-112 1.012 crystals m.p. 87-88 1.013 crystals m.p.112-114 1.014 oil 1.021 crystals m.p. 128-129 1.023 crystals m.p. 91-921.024 oil 1.026 amorphous 1.028 amorphous 1.03  resin 1.031 crystalsm.p. 145-146 1.042 oil 1.043 crystals m.p. 107-110 1.047 crystals m.p.155-156 1.048 viscous 1.05  crystals m.p. 51-53 1.06  crystals m.p. >2201.109 oil 1.195 oil 1.258 crystals m.p. 119-121 1.31  crystals m.p.92-94 1.312 viscous 1.313 crystals m.p. 137-138 1.314 oil 1.316 resin1.323 oil 1.334 resin 1.335 crystals m.p. 140-142 1.339 crystals m.p.137-139 1.341 resin 1.343 crystals m.p. 97-99 1.347 crystals m.p.135-137 1.349 oil, n_(D) 1.4965 1.351 crystals m.p. 125-127 1.353 resin,n_(D) 1.5289 1.355 crystals m.p. 90-92 1.356 resin 1.358 resin 1.361 oil1.362 crystals m.p. 139-142 1.371 crystals m.p. 96-97 1.372 resin 1.373resin 1.374 crystals m.p. 116-1199 1.375 resin 1.376 crystals m.p. >2701.381 crystals m.p. 117-118 1.383 crystals m.p. 172-173 1.384 resin1.385 resin 1.386 resin 1.387 resin 1.388 crystals m.p. 102-104 1.389crystals m.p. 143-145 1.39  crystals m.p. 195-197 1.391 solid 1.392crystals m.p. 202-206 1.398 crystals m.p. 137-138 1.399 crystals m.p.262-263 1.4  oil 1.401 oil 1.402 oil 1.403 oil 1.404 oil 1.405 viscous1.406 oil 1.408 oil 1.409 oil 1.41  oil 1.411 crystals m.p. 98-100 1.412crystals m.p. 130-131 1.413 crystals m.p. 167-170 1.414 crystals m.p.166-167 1.415 crystals m.p. 91-93 1.418 crystals m.p. 149-150 1.421crystals m.p. 88-89 1.422 crystals m.p. 175-177 1.423 crystals m.p.45-47 1.424 crystals m.p. 102-104 2.001 resin 2.003 oil 2.03  crystalsm.p. 107-110 2.038 crystals m.p. 111-113 2.043 resin 2.044 crystals m.p.105-106 2.045 amorphous 3.001 crystals m.p. 95-97 3.054 oil 3.055crystals m.p. 108-110 3.056 resin, D_(D) 1.5509 4.009 crystals m.p.107-109 4.01  oil 4.011 oil 4.014 crystals m.p. 148-149 4.021 crystalsm.p. 44-45 4.033 crystals m.p. 46-48 4.124 crystals m.p. 46-48 4.328 oil5.008 resin 5.081 resin 5.083 crystals m.p. 161-162 5.084 crystals m.p.215-216 5.085 resin 6.006 crystals m.p. 176-177 6.041 crystals m.p.186-187 6.076 crystals m.p. 195-196 6.111 crystals m.p. 163-164 7.009ratio A: B = 2:1. H-NMR(CDCl₃,ppm) SCH₃: A: 2.50; B: 2.66. 7.01  ratioA: B = 5:1. H-NMR(CDCl₃,ppm) SCH₃: A: 2.50; B: 2.64. 7.011 ratio A: B =9:1. H-NMR(CDCl₃,ppm) SCH₃: A: 2.46; B: 2.59. 7.021 ratio A: B = 3:1.H-NMR(CDCl₃,ppm) SCH₃: A: 2.50; B: 2.62. 7.18  ratio A: B = 2:.H-NMR(CDCl₃,ppm) SO₂CH₃: A: 3.40; B: 3.58. 7.182 ratio A: B = 9:1.H-NMR(CDCl₃,ppm) SO₂CH₃: A: 3.32; B: 3.50. 7.192 ratio A: B = 3:1.H-NMR(CDCl₃,ppm) SO₂CH₃: A: 3.40; B: 3.58. 8.009 crystals m.p. 96-978.01  amorphous 8.011 oil 8.021 oil 9.009 crystals m.p. 112-113 9.01 amorphous 9.011 amorphous 9.021 oil

Biological Examples Example B1 Herbical action before emergence of theplants (pre-emergence action)

Monocotyledonous and dicotyledonous test plants are sown in standardsoil in plastic pots. Immediately after sowing, the test substances aresprayed on (500 l of water/ha) as an aqueous suspension (prepared from a25% wettable powder (Example F3, b) according to WO 97/34485) oremulsion (prepared from a 25% emulsion concentrate (Example F1, c)),corresponding to a dosage of 2 kg of AS/ha. The test plants are thengrown under optimum conditions in a greenhouse. After a test period of 3weeks, the test is evaluated with a nine-level scale of ratings(1=complete damage, 9=no effect). Ratings of 1 to 4 (in particular 1 to3) mean good to very good herbicidal action.

TABLE B1 pre-emergence action: Active compound Test plant No. AvenaCyperus Setaria Sinapis Solanum Stellaria 1.009 2 1 1 2 1 2 1.376 2 1 12 1 2 4.009 1 2 1 2 1 3 7.009 4 2 1 3 1 2 1.381 4 1 2 2 1 1 1.011 2 1 11 1 1 5.008 2 1 1 2 1 2 4.021 2 1 2 2 1 2 1.010 2 1 1 1 1 2 1.021 4 2 11 1 3 1.398 2 1 1 1 1 1 1.195 2 1 1 1 1 2 4.124 2 1 2 2 1 2 1.411 3 2 12 1 2 1.042 4 2 2 1 1 4 1.023 2 2 2 1 1 2 1.109 2 2 2 2 1 3 1.313 3 1 21 1 2 1.401 2 1 1 2 1 2 1.404 2 1 1 2 1 2 1.400 2 1 1 2 1 2 1.403 2 1 11 1 2 1.405 2 1 1 1 1 2 1.406 2 1 1 1 1 2 1.402 2 1 1 2 1 2 1.005 4 1 11 1 1 1.043 4 2 1 2 1 2 1.409 1 1 1 1 1 1 1.41  2 1 1 1 1 1 1.06  2 1 12 1 1 7.192 4 2 2 3 2 2 7.021 1 1 1 1 1 1

The same results are obtained when the compounds of the formula I areformulated according to Examples F2 and F4 to F8 according to WO97/34485.

Example B2 Post-emeroence Herbicidal Action

Monocotyledonous and dicotyledonous test plants are grown in plasticpots with standard soil in a greenhouse and, in the 4- to 6-leaf stage,are sprayed with an aqueous suspension of the test substances of theformula 1, prepared from a 25% wettable powder (Example F3, b) accordingto WO 97134485) or with an emulsion of the test substances of theformula I, prepared from a 25% emulsion concentrate (Example F1, c)according to WO 97/34485), corresponding to a dosage of 2 kg of AS/ha(500 l of water/ha). The test plants are then grown further underoptimum conditions in a greenhouse. After a test period of about 18days, the test is evaluated with a nine-level scale of rating(1=complete damage, 9=no effect). Ratings of 1 to 4 (in particular 1 to3) mean good to very good herbicidal action. In this test, the compoundsof the formula I show strong herbicidal action.

TABLE B2 post-emergence action: Active compound Test plant No. AvenaSetaria Solanum Sinapis Stellaria 1.009 1 1 1 1 2 1.376 1 2 2 1 2 4.0091 1 1 1 1 1.026 3 1 1 1 2 7.009 3 2 1 1 1 1.381 2 2 2 2 2 1.011 2 2 2 22 5.008 2 3 1 1 2 5.085 3 2 2 1 2 4.021 2 2 1 1 2 1.012 3 2 2 1 2 1.0102 2 2 1 4 4.010 3 3 2 2 2 1.021 2 4 2 1 2 1.398 2 2 2 1 2 1.195 2 2 2 12 4.124 2 2 1 1 2 1.411 2 2 2 1 2 1.008 2 2 2 1 2 6.006 2 5 2 2 2 5.0813 2 1 1 2 1.042 2 2 2 1 2 1.023 2 2 2 1 2 1.109 2 2 2 1 2 1.313 2 2 2 12 1.401 2 2 2 2 2 1.404 2 2 1 1 2 1.400 2 2 2 1 2 1.403 2 2 2 1 2 1.4032 2 2 1 2 1.405 2 2 2 1 2 1.406 2 2 1 1 2 1.402 2 2 2 1 2 1.001 3 2 2 12 1.005 2 2 2 1 2 1.362 3 2 2 1 2 1.043 2 2 2 1 2 1.409 2 1 1 1 2 1.4101 1 1 1 1 1.060 2 1 1 1 2 7.192 2 3 3 2 2 7.021 1 2 1 1 2 1.048 2 1 1 12

The same results are obtained when the compounds of the formula I areformulated according to Examples F2 and F4 to F8 according to WO97/34485.

Example B3 Herbicidal action before emergence of the plants(pre-emergence action)

Monocotyledonous and dicotyledonous test plants are sown in pots instandard soil. Immediately after sowing, the test substances are sprayedon (500 l of spray liquorlha) as an aqueous suspension, prepared from awettable powder WP10 corresponding to the desired dosage (250 g ofa.i./ha).

The test plants are then grown under optimum conditions in a greenhouse.After a test period of 3 weeks, the test is evaluated with a nine -evelscale of ratings (1=complete damage, 9=no effect). Ratings of 1 to 4 (inparticular 1 to 3) mean good to very good herbicidal action, 7-9 meangood tolerance.

TABLE B3 Pre-emergence action: Test plant Active Dose compound Abut-Amar- Cheno- [g of No. ilon anthus podium Kochia Sida Stellaria AS/ha]1.355 1 1 1 1 2 2 250 1.347 2 2 1 1 4 1 250 1.335 1 2 1 5 2 7 250 1.3491 3 1 4 2 5 250 1.339 2 1 1 7 2 1 250 1.341 3 9 1 9 4 1 250 1.343 1 4 19 3 5 250

The same results are obtained when the compounds of the formula I areformulated according to Examples F2 and F4 to F8 according to WO97/34485.

Example B4 Herbicidal action after the emergence of the plants (post-emer gence action)

Monocotyledonous and dicotyledonous test plants are sown in pots instandard soil. In the 2-3- leaf stage of the test plants, the testsubstances are sprayed on (500 l of spray liquor/ha) as an aqueoussuspension, prepared from a wettable powder WP10 according to thedesired dosage (250 g of a.i./ha). 0.2% of X77 is added as wetting agentto the spray liquor. The test plants are then grown under optimumconditions in a greenhouse.

After a test period of 3 weeks, the test is evaluated with a nine4evelscale of ratings (1=complete damage, 9=no effect). Ratings of 1 to 4 (inparticular 1 to 3) mean good to very good herbicidal action, 7-9 meangood tolerance.

TABLE B4 Post-emergence action: Test plant Active Dose compound Abut-Amar- Cheno- [g of No. ilon anthus podium Kochia Sida Stellaria AS/ha]1.355 2 2 2 3 2 3 250 1.347 3 2 2 2 3 3 250 1.335 3 2 2 2 2 3 250 1.3492 2 2 2 2 3 250 1.339 2 2 3 1 4 3 250 1.351 5 2 3 3 3 3 250 1.341 5 2 34 5 4 250 1.343 3 2 2 3 9 3 250 1.361 2 2 2 2 2 3 250

The same results are obtained when the compounds of the formula I areformulated according to Examples F2 and F4 to F8 according to WO97/34485.

What is claimed is:
 1. A compound of the formula I

in which each R independently is C₁-C₆alkyl, C₁-C₆alkenyl,C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆ haloalkynyl, C₃-C₆cycloalkyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkyl, C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkoxycarbonyl,C₁-C₆alkylcarbonyl, C₁-C₆alkylamino, di-C₁-C₆ alkylamino,C₁-C₆alkylaminosulfonyl, di-C₁-C₆alkylaminosulfonyl, —N(R₁)—S—R₂,—N(R₃)—SO—R₄, —N(R₅)—SO₂—R₆, nitro, cyano, halogen, hydroxyl, amino,formyl, hydroxy-C₁-C₆alkyl, C₁-C₆ alkoxy-C₁-C₆alkyl,C₁-C₆alkoxycarbonyloxy-C₁-C₆alkyl, C₁-C₆alkytthio-C₁-C₆alkyl, C₁-C₆alkylsulfinyl-C₁-C₆alkyl, C₁-C₆alkylsulfonyl-C₁-C₆alkyl,thiocyanato-C₁-C₆alkyl, cyano-C₁-C₆ alkyl, oxiranyl, C₃-C₆alkenyloxy,C₃-C₆alkynyloxy, C₁-C₆alkoxy-C₁-C₆alkoxy, cyano-C₁-C₆ alkenyloxy,C₁-C₆alkoxycarbonyloxy-C₁-C₆alkoxy, C₃-C₆alkynyloxy, cyano-C₁-C₆lkoxy,C₁-C₆ alkoxycarbonyl-C₁-C₆alkoxy, C₁-C₆alkylthio-C₁-C₆alkoxy,alkoxycarbonyl-C₁-C₆alkylthio, alkoxycarbonyl-C₁-C₆alkylsulfinyl,alkoxycarbonyl-C₁-C₆alkylsulfonyl, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, phenyl, benzyl, phenoxy, phenylthio,phenylsulfinyl, phenylsulfonyl, benzylthio, benzylsulfinyl orbenzylsulfonyl, where the phenyl groups may be mono- or polysubs ttutedby halogen, methyl, ethyl, trifluoromethyl, methoxy or nitro, or R is afive- to ten-membered monocyclic or fused bicyclic ring system, whichmay be aromatic or partially saturated and may contain 1 to 4heteroatoms selected from the group consisting of nitrogen, oxygen andsulfur, where the ring system is either attached directly to thepyridine ring or attached to the pyridine ring via a C₁-C₄alkylenegroup, and where each ring system may not contain more than 2 oxygenatoms and not more than two sulfur atoms, and where the ring system forits part may be mono-, di- or trisubstituted by C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl,C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆ haloalkoxy, C₃-C₆alkenyloxy,C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₃-C₆alkeny fthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio,C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₇, NR₈R₉,halogen, cyano, nitro, phenyl and benzylthio, where phenyl andbenzylthio for their part may be substituted on the phenyl ring byC₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyanoor nitro, and where substituents on the nitrogen in the heterocyclicring are different from halogen; m is 1, 2,3 or 4; p is 0 or 1; R₁, R₃and R₅ independently of one another are hydrogen or C₁-C₆alkyl; R₂ isNR₁₀R₁₁, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆alkenyl, C₃-C6 haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl,C₃-C₆cycloalkyl or phenyl, where phenyl for its part may be substitutedby C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen,cyano or nitro; R₄ is NR₁₂R₁₃, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆ haloalkenyl, C₃-C₆alkynyl,C₃-C₆haloalkynyl, C₃-C₆cycloalkyl or phenyl, where phenyl for its partmay be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro; R₆is NR₁₄R₁₅, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₈haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₃-C₆cycloalkyl or phenyl,where phenyl for its part may be substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;R₇ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for itspart may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro; R₈, R₁₀, R₁₂ and R₁₄independently of one another are hydrogen or C₁-C₆alkyl; R₉, R₁₁, R₁₃and R₁₅ independently of one another are C₁-C₆alkyl or C₁-C₆alkoxy; Q isthe group Q₁

in which R₁₆, R₁₇, R₁₈ and R₁₉ independently of one another arehydrogen, hydroxyl, C₁-C₄alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl,C₁-C₄alkoxycarbonyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₄alkyl-NHS(O)₂, C₁-C₄haloalkyl, —NH—C₁-C₄alkyl,—N(C₁-C₄alkyl)₂, C₁-C₆ alkoxy, cyano, nitro, halogen or phenyl, whichfor its part may be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₄alkyl-S(O)₂O,C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C_(l)-C₄ haloalkylsulfonyl,C₁-C₄haloalkyl-S(O)₂O, C₁-C₄aIkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro, COOH or cyano; or two adjacent substituents fromthe group consisting of R₁₆, R₁₇, R₁₈ and R₁₉ form a C₂-C₆alkylenebridge; R₂₀ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy,C₁-C₄alkoxycarbonyl-C₁-C₄ alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl,C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂ haloalkylsulfinyl,C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₂-C₁₂alkenylthio,C₂-C₁₂alkenylsulfinyl, C₂-C₁₂ alkenylsulfonyl, C₂-C₁₂alkynylthio,C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl, C₂-C₁₂ haloalkenylthio,C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂haloalkenylsulfonyl,C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O,C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₃₇R₃₈N, R₇₁R₇₂NNH—,R₂₁R₂₂NC(O)O—, R₇₃R₇₄NC(O)NH—, C₁-C₄alkyl-S(O)₂NR₃₉, C₁-C₄haloalkyl-S(O)₂NR₄₀, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O,C₁-C₁₈alkylcarbonyloxy, where the alkyl group may be substituted byhalogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, C₂-C₁₈alkenylcarbonyloxy,C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl,C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)—NH—,di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)—NH—, benzyloxy, benzylthio,benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl,phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groupsfor their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄hatoalkylthio,C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O,C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄ alkyl), halogen, nitro orcyano, or a group Ar₁-thio, Ar₂-sulfinyl, Ar₃-sulfonyl, —OCO—Ar₄ orNH—Ar₅ in which Ar₁, Ar₂, Ar₃, Ar₄ and Ar₅ independently of one anotherare a five- to ten-membered monocyclic or fused bicyclic ring systemwhich may be aromatic or partially saturated and may contain 1 to 4heteroatoms selected from the group consisting of nitrogen, oxygen andsulfur, and in which each ring system may not contain more than 2 oxygenatoms and not more than two sulfur atoms, and in which the ring systemfor its part may be mono-, di- or trisubstituted by C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl,C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy,C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₃-C₆alkenylthio, C₃₋-C₆haloalkenylthio, C₃-C₆alkyny fthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio,C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl,C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₄₁,NR₄₂R₄₃, halogen, cyano, nitro, phenyl and benzylthio, where phenyl andbenzylthio for their part may be substituted on the phenyl ring byC₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyanoor nitro, and where substituents on the nitrogen in the heterocyclicring are different from halogen; R₄₁ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl or phenyl,where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; R₄₂ ishydrogen or C₁-C₆alkyl; R₄₃ is C₁-C₆alkyl or C₁-C₆alkoxy; R₂₁, R₃₇, R₃₉,R₄₀, R₇₁ and R₇₃ independently of one another are hydrogen orC₁-C₄alkyl; R₂₂, R₃₈, R₇₂ and R₇₄ independently of one another arehydrogen, C₁-C₁₂alkyl, hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy orC₃-C₆alkynyloxy; or R₂₁ and R₂₂ together or R₃₇ and R₃₈ together or R₇₁and R₇₂ together or R₇₃ and R₇₄ together are pyrrolidino, piperidino,morpholino, thiomorpholino, which may be mono- or polysubstituted bymethyl groups; or are the group Q₂

in which Y is a chemical bond, an alkylene group A l, carbonyl, oxygen,sulfur, sulfinyl, suifonyl, —NHR₂₄₈ or NH(CO)R₂₄₉; A₁ is C(R₂₄₆R₂₄₇)m₀₁;A is C(R₂₄₄R₂₄₅)r; r and m₀₁ independently of one another are 1 or 2;R₂₄₀ is hydrogen, methyl or C₁-C₃alkoxycarbonyl; R₂₄₁, R₂₄₂, R₂₄₃, R₂₄₄,R₂₄₅, R₂₄₆ and R₂₄₇ independently of one another are hydrogen, halogenor methyl, or R₂₄₃ together with an adjacent group R₂₄₅ or R₂₄₇ is achemical bond; R₂₄₈ and R₂₄₉ independently of one another are hydrogenor C₁-C₄alkyl; R₂₃ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN,C₁-C₁₂alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₄ alkoxy, C₁-C₁₂alkylthio,C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio,C₁-C₆alkoxy-C₁-C₆ alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl,C₂-C₁₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂ alkenylsulfonyl,C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl, C₂-C₁₂haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂haloalkenylsulfonyl,C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₄₄R₄₅N, R₇₅R₇₆NNH—,R₄₆R₄₇NC(O)O—, R₇₇R₇₈NC(O)NH—, C₁-C₄alkyl-S(O)₂NR₄₈, C₁-C₄haloalkyl-S(O)₂NR₄₉, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O,C₁-C₁₈alkylcarbonyloxy, where the alkyl group may be substituted byhalogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, C₂-C₁₈alkenylcarbonyloxy,C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyioxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl,C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)—NH—,di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)—NH—, benzyloxy, benzylthio,benzyisulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl,phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groupsfor their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio,C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O,C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄ alkyl), halogen, nitro orcyano, or a group Ar₆-thio, Arrsulfinyl, Ar₈-sulfonyl, —OCO—Ar₉ orNH—Ar₁₀ in which Ar₆, Ar₇, Ar₈, Ar₉ and Ar₁₀ independently of oneanother are a five- to ten-membered monocyclic or fused bicyclic ringsystem which may be aromatic or partially saturated and may contain 1 to4 heteroatoms selected from the group consisting of nitrogen, oxygen andsulfur, and in which each ring system may not contain more than 2 oxygenatoms and not more than two sulfur atoms, and in which the ring systemfor its part may be mono-, di- or trisubstituted by C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl,C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy,C₃-C₆alkyny toxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio,C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl,C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₅₀,NR₅₁R₅₂, halogen, cyano, nitro, phenyl and benzylthio, where phenyl andbenzylthio for their part may be substituted on the phenyl ring byC₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyanoor nitro, and where substituents on the nitrogen in the heterocyclicring are different from halogen; R₅₀ is C₁-C₃alkoxy,C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may besubstituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro; R₅₁ is hydrogen or C₁-C₆alkyl;R₅₂ is C₁-C₆alkyl or C₁-C₆alkoxy; R₄₆, R₄₄, R₄₈, R₄₉, R₇₅ and R₇₇independently of one another are hydrogen or C₁-C₄alkyl; R₄₇, R₄₅, R₇₆and R₇₈ independently of one another are hydrogen, C₁-C₁₂alkyl,hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy; or R₄₄ andR₄₅ together or R₄₆ and R₄₇ together or R₇₅ and R₇₆ together or R₇₇ andR₇₈ together are pyrro tidino, piperidino, morpholino, thiomorpholino,which may be mono- or polysubstituted by methyl groups; or are the groupQ₃

in which R₂ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy,C₁-C₄alkoxycarbonyl-C₁-C₄ alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl,C₁-C₁₂alkylsulfonyl, C₁-C₁ ₂haloalkylthio, C₁-C₁₂ haloalkylsulfinyl,C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₂-C₁ ₂alkenylthio,C₂-C₁₂alkenylsulfinyl, C₂-C₁₂ alkenylsulfonyl, C₂-C₁₂alkynylthio,C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl, C₂-C₁₂ haloalkenylthio,C₂-C₁₂haloalkenyisulfinyl, C₁-C₁₂haloalkenylsulfonyl,C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O,C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₅₃R₅₄N, R₇₉R₈₀NNH—,R₅₅R₅₆NC(O)O—, R₈₁R₈₂NC(O)NH—, C₁-C₄alkyl-S(O)₂NR₅₇, C₁-C₄haloalkyl-S(O)₂NR₅₈, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O,C₁-C₁₈alkylcarbonyloxy, where the alkyl group may be substituted byhalogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, C₂-C₁₈alkenyicarbonyloxy,C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl,C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)—NH—,di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)—NH—, benzyloxy, benzylthio,benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl,phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groupsfor their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio,C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O,C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄ alkyl), halogen, nitro orcyano, or a group Ar₁₁-thio, Ar₁₂-sulfinyl, Ar₁₃-sulfonyl, —OCO—Ar₁₄ orNH—Ar₁₅ in which Ar₁₁, Ar₁₂, Ar₁₃, Ar₁₄ and Ar₁₅ independently of oneanother are a five- to ten-membered monocyclic or fused bicyclic ringsystem which may be aromatic or partially saturated and may contain 1 to4 heteroatoms selected from the group consisting of nitrogen, oxygen andsulfur, and in which each ring system may not contain more than 2 oxygenatoms and not more than two sulfur atoms, and in which the ring systemfor its part may be mono-, di- or trisubstituted by C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl,C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy,C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio,C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsu ffonyl, aminosulfonyl,C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₅₉,NR₆₀R₆₁, halogen, cyano, nitro, phenyl and benzylthio, where phenyl andbenzylthio for their part may be substituted on the phenyl ring byC₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyanoor nitro, and where substituents on the nitrogen in the heterocyclicring are different from halogen; R₅₉ is C₁-C₃alkoxy,C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may besubstituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro; R₆₀ is hydrogen or C₁-C₆alkyl;R₆₁ is C₁-C₆alkyl or C₁-C₆alkoxy; R₅₅, R₅₃, R₅₇, R₅₈, R₇₉ and R₈₁independently of one another are hydrogen or C₁-C₄alkyl; R₅₆, R₅₄, R₈₀and R₈₂ independently of one another are hydrogen, C₁-C₁₂alkyl,hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy; or R₅₃ andR₅₄ together or R₅₅ and R₅₆ together or R₇₉ and R₈₀ together or R₈₁ andR₈₂ together are pyrrolidino, piperidino, morpholino, thiomorpholino,which may be mono- or polysubstituted by methyl groups; R₂₉ is hydrogen,C₁-C₆alkyl, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, (C₁-C₄alkyl)NHCO,phenylaminocarbonyl, benzylaminocarbonyl or (C₁-C₄alkyl)₂NCO, where thephenyl and benzyl groups for their part may each be substituted byC₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,C₁-C₄alkyl-S(O)₂O, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl,C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄ alkyl-S(O)₂NH,C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano; or is the groupQ₄

in which R₃₀ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy,C₁-C₄alkoxycarbonyl-C₁-C₄ alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl,C₁-C₁ ₂alkyisulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂ haloalkylsulfinyl,C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆alkylsu ifinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₂-C₁ ₂alkenylthio,C₂-C₁₂alkenylsulfinyl, C₂-C₁₂ alkenylsulfonyl, C₂-C₁₂alkynylthio,C₂-C₁₂alkynylsulfinyl, C₂-C₂alkynylsulfonyl, C₂-C₁₂ haloalkenylthio,C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂haloalkenylsulfonyl,C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl,C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O,C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₆₂R₆₃N, R₈₃R₈₄NNH—,R₆₄R₆₅NC(O)—, R₈₅R₈₆NC(O)NH—, C₁-C₄alkyl-S(O)₂NR₆₆, C₁-C₄haloalkyl-S(O)₂NR₆₇, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, where the alkyl group may be substituted by halogen,C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, C₂-C₁₈alkenylcarbonyloxy,C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl,C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)—NH—,di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)—NH—, benzyloxy, benzylthio,benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl,phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groupsfor their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl,C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio,C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O,C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄ alkyl), halogen, nitro orcyano, or a group Ar₁₆-thio, Ar₁₇sulfinyl, Ar₁₈-sulfonyl, —OCO—Ar₁₉ orNH—Ar₂₀ in which Ar₁₆, Ar₁₇, Ar₁₈, Ar₁₉ and Ar₂₀ independently of oneanother are a five- to ten-me mbered monocyclic or fused bicyclic ringsystem which may be aromatic or partially saturated and may contain 1 to4 heteroatoms selected from the group consisting of nitrogen, oxygen andsulfur, and in which each ring system may not contain more than 2 oxygenatoms and not more than two sulfur atoms, and in which the ring systemfor its part may be mono-, di- or trisubstituted by C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl,C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy,C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio,C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,C₁-C₆alkylsulfonyl, C ,-C₆haioalkyisulfonyl, aminosulfonyl,C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₆₈,NR₆₉R₇₀, halogen, cyano, nitro, phenyl and benzylthio, where phenyl andbenzylthio for their part may be substituted on the phenyl ring byC₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyanoor nitro, and where substituents on the nitrogen in the heterocyclicring are different from halogen; R₆₈ is C₁-C₃alkoxy,C₂C₄alkoxycarbonylt, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may besubstituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy,C₁-C₃haloalkoxy, halogen, cyano or nitro; R₇₀ is hydrogen or C₁-C₆alkyl;R₆₁ is C₁-C₆alkyl or C₁-C₆alkoxy; R₆₄, R₆₂, R₆₆, R₆₇, R₈₃ and R₈₅independently of one another are hydrogen or C₁-C₄alkyl; R₆₅, R₆₃, R₈₄and R₈₆ independently of one another are hydrogen, C₁-C₁₂alkyl,hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy; or R₆₂ andR₆₃ together or R₆₄ and R₆₅ together or R₈₃ and R₈₄ together or R₈₅ andR₈₆ together are pyrrolidino, piperidino, morpholino, thiomorpholino,which may be mono- or polysubstituted by methyl groups; R₃₃ and R₃₄independently of one another are hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl,C₂-C₆ alkynyl, C₁-C₄alkoxycarbonyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₄ alkyl-NHS(O)₂, C₁-C₄haloalkyl, —NH—C₁-C₄alkyl,—N(C₁-C₄alkyl )₂, C₁-C₆alkoxy or phenyl, which for its part may besubstituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino,di-C₁-C₄alkylamino, C₁-C₆ alkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O,C₁-C₄alkyl-S(O)₂NH, C₁-C₄ alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro, COOHor cyano; or R₃₃ and R₃₄ together forrn a C₂-C₆alkylene bridge; and R₃₅is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl or benzyl, which forits part may be substituted by halogen, methyl or methoxy, or isC₁-C₄alkoxycarbonyl or phenyl, which for its part may be substituted byC₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino,di-C₁-C₄alkylamino, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-c₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O,C₁-C₄alkyl-S(O)₂NH, C₁-C₄ alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro, COOHor cyano; or is the group Q₅

in which Z is S, SO or SO₂; R₀₁ is hydrogen, C₁-C₈alkyl, C₁-C₈alkylsubstituted by halogen, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl,C₁-C₄alkylsulfinyl, —CO₂R₀₂, —COR₀₃, —COSR₀₄, —NR₀₅R₀₆, CONR₀₃₆R₀₃₇ orphenyl, which for its part may be substituted by C₁-C₄alkyl,C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl,C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano,—COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄ alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄ aikyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl,N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl,N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl, N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl,OSO₂—C₁-C₄alkyl, CONR₂₅R₂₆, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl,C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsulfonyl,C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl,C₁-C₄haloalkylsulfinyl, phenylsulfinyl, C₁-C₄alkylene-phenyl or—NR₀₁₅CO₂R₀₂₇; or R₀₁ is C₂-C₈alkenyl or C₂-C₈alkenyl substituted byhalogen, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl,C₁-C₄alkylsulfinyl, —CONR₀₃₂R₀₃₃, cyano, nitro, —CHO, —CO₂R₀₃₈, —COR₀₃₉,—COS—C₁-C₄alkyl, —NR₀₃₄R₀₃₅ or phenyl which for its part may besubstituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen,nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alky fthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄ alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl, N(C₂-Cralkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl,N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄ alkyl,N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl,N(phenyl)SO₂-phenyl, OSO₂-C₁-C₄alkyl, CONR₀₄₀R₀₄₁, OSO₂—C₁-C₄haloalkyl,OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄ haioalkylthio, phenylthio,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl,C₁-C₄alkylene-phenyl or —NR₀₄₃CO₂R₀₄₂; or R₀₁ is C₃-C₆alkynyl orC₃-C₆alkynyl substituted by halogen, C₁-C₄haloalkyl, cyano, —CO₂R₀₄₄ orphenyl, which for its part may be substituted by C₁-C₄alkyl,C₁-C₆haloalkyl, C_(l)-C₄ alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl,C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano,—COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄ alkylsulfonyl)-C₁-C₄alkyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl,N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl,N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl,N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl,N(phenyl)SO₂-phenyl, OS₂O-C₁-C₄ alkyl, CONR₀₂₈R₀₂₉, OSO₂—C₁-C₄haloalkyl,OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl,C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl,C₁-C₄alkylene-phenyl or —NR₀₃₁CO₂R₀₃₀; or R₀₁ is C₃-C₇cycloalkyl,C₃-C₁cycloalkyl substituted by C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄ alkylthio,C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl or phenyl, which for its part maybe substituted by halogen, nitro, cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkyl and C₁-C₄haloalkyl; orR₀₁ is C₁-C₄alkylene-C₃-C₇cycloalkyl, phenyl, or phenyl which issubstituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen,nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsul fonyl)-C₁-C₄alkyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂-C₁-C₄ alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl,N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl,N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄ alkyl,N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl,N(phenyl)SO₂-phenyl, OSO₂—C₁-C₄alkyl, CONR₀₄₅R₀₄₆, OSO₂—C₁-C₄haloalkyl,OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, phenylthio,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, or —NR₀₄₈CO₂R₀₄₇;or R₀₁ is C₁-C₄alkylene-phenyl, COR₀₇ or 4-6-membered heterocyclyl; R₀₂,R₀₃₈, R₀₄₄ and R₀₆₆ independently of one another are hydrogen,C₁-C₄alkyl, phenyl, or phenyl which is substituted by C₁-C₄alkyl,C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl,C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano,—COOH, COOC₁-C₄alkyl, Coophenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄ alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyi)-C₁-C₄alkyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆ alkenyl)SO₂—C₁-C₄alkyl,N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl,N(C₃-C₇Cyloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl,N(phenyl)SO₂-phenyl, OSO₂-C₁-C₄alkyl, CONR₀₄₉R₀₅₀, OSO₂—C₁-C₄ haloalkyl,OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl,C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl,C₁-C₄alkylene-phenyl or —NR₀₅₂CO₂R₀₅₃; R₀₃, R₀₃₉ and R₀₆₇ independentlyof one another are C₁-C₄alkyl, phenyl or phenyl which is substituted byC₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl,C₃-C₆ alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano,—COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl,N(C₂-C₆alkenyl)S)₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl,N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇ cycloalkyl)SO₂—C₁-C₄alkyl,N(C₃-₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂-C₁-C₄alkyl,N(phenyl)SO₂-phenyl, OSO₂-C₁-C₄alkyl, CONR₀₇₀R₀₅₄, OSO₂—C₁-C₄haloalkyl,OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl,C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl,C₁-C₄alkylene-phenyl or —NR₀₅₆CO₂R₀₅₅; R₀₄ is C₁-C₄alkyl; R₀₅ ishydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇cycloalkyl,phenyl or phenyl which is substituted by C₁-C₄alkyl, C₁-C₆haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆ alkenyl, C₃-C₆alkynyl,C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH,COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄ alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆ alkenyl)SO₂—C₁-C₄alkyl,N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂H, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂phenyl,N(C₃-C₇cycloalkyl)SO₂H, N(C₃-C₇ cycloalkyl)SO₂—C₁-C₄alkyl,N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl,N(phenyl)SO₂-phenyl, OSO₂-C₁-C₄alkyl, CONR₀₅₇R₀₅₈, OSO₂—C₁-C₄haloalkyl,OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄ha hoalkylthio, phenylthio,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl,C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl,C₁-C₄alkylenephenyl or —NR₀₆₀CO₂R₀₅₉; R₀₆ is hydrogen, C₁-C₄alkyl,C₂-C₆aikenyl, C₃-C₆alkynyl, C₃-C₇cycloalkyl, phenyl or phenyl which issubstituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₂-C₆ alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkyny loxy, halogen,nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy,(C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄ alkylthio)-C₁-C₄alkyl,(C₁-C₄alkylsulfinyl)C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl,NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alky l,N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆ alkenyl)SO₂—C₁-C₄alkyl,N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl,N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl,N(phenyl)SO₂-phenyl, OS₀ ₂-C₁-C₄alkyl, CONR₀₆₁R₀₆₂, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl,C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl,C₁-C₄alkylene-phenyl or —NR₀₆₄CO₂R₀₆₃; R₀₇ is phenyl, substitutedphenyl, C₁-C₄alkyl, C₁-C₄alkoxy or —NR₀₈R₀₉; R₀₈ and R₀₉ independentlyof one another are C₁-C₄alkyl, phenyl or phenyl which is substituted byhalogen, nitro, cyano, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄thioalkyl,—CO₂R₀₆₆, —COR₀₆₇, C₁-C₄alkylsulfonyl, C₁-C₄alkylsulfinyl,C₁-C₄haloalkyl; or R₀₈ and R₀₉ together form a 5-6-membered ring whichmay be interrupted by oxygen, NR₀₆₅ or S, R₀₁₅, R₀₃₁, R₀₄₃, R₀₄₈, R₀₅₂,R₀₅₆, R₀₆₀ and R₀₆₄ independently of one another are hydrogen,C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl or C₃-C₇cycloalkyl; R₀₂₅, R₀₂₆,R₀₂₇, R₀₂₈, R₀₂₉, R₀₃₀, R₀₃₂, R₀₃₃, R₀₃₄, R₀₃₅, R₀₃₆, R₀₃₇, R₀₄₀, R₀₄₁,R₀₄₂, R₀₄₅, R₀₄₆, R₀₄₇, R₀₄₉, R₀₅₀, R₀₅₃, R₀₅₄, R₀₅₅, R₀₅₇, R₀₅₈, R₀₅₉,R₀₆₁, R₀₆₂, R₀₆₃, R₀₆₅ and R₀₇₀ independently of one another arehydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇cycloalkyl,phenyl, or phenyl which is substituted by halogen, nitro, cyano,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄ alkylthio, C₁-C₄haloalkylthio,C₁-C₄alkyl or C₁-C₄haloalkyl; and R₃₆ is C₁-C₄alkyl, C₁-C₄haloalkyl,C₃-C₆alkenyl, C₃C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆ haloalkynyl,C₃-C₆cycloalkyl or C₃-C₆cycloalkyl which is substituted by halogen,C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆aIkynyl, C₃-C₆haloalkynyt, C₁-C₄ alkoxycarbonyl, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylthio,C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylcarbonyl,di-C₁-C₄alkylamino, C₁-C₄ alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkyl-S(O)₂O,C₁-C₄haloalkyl-S(O)₂O or phenyl which for its part may be substituted byhalogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, cyano,nitro or COOH; and agronomically acceptable salts M⁺ and allstereoisomers and tautomers of the compounds of the formula I.
 2. Aherbicidal and plant-growth-inhibiting composition, which contains aherbicidally effective amount of a compound of the formula I, accordingto claim 1, on an inert carrier.
 3. A method for controlling undesirableplant growth, wherein a herbicidally effective amount of an activecompound of the formula I, according to claim 1, or a composition whichcontains this active compound is applied to the plants or their habitat.4. A method for inhibiting plant growth, wherein a herbicidallyeffective amount of an active compound of the formula I, according toclaim 1, or a composition which contains this active compound is appliedto the plants or their habitat.